Oxime ether derivative and fungicide for agricultural and horticultural use

ABSTRACT

The present invention provides a novel oxime ether derivative represented by the following formula (I), or salt thereof, that can be industrially produced advantageously, and can function as a fungicide for agricultural and horticultural use that has reliable effects and can be used safely, and a fungicide for agricultural and horticultural use that contains at least one of these compounds as an active ingredient thereof. In addition, the present invention provides a novel ketone derivative that is a production intermediate of the oxime ether derivative.

This application is a national phase application of PCT/JP2008/003717,filed on Dec. 11, 2008, which claims priority under 35 U.S.C. 119 toJapanese Patent Application Nos. 2007-319111 filed Dec. 11, 2007.

TECHNICAL FIELD

The present invention relates to a novel oxime ether derivative and saltthereof, and to a fungicide for agricultural and horticultural use thatcontains at least one of these compounds as an active ingredientthereof.

The present application claims priority on Japanese Patent ApplicationNo. 2007-319111, filed in Japan on Dec. 11, 2007, the content of whichis incorporated herein by reference.

BACKGROUND ART

Patent Document 1 described below discloses, in relation to the presentinvention, an oxime ether derivative (A), which has a chemical structureas indicated below that resembles the oxime ether derivative compound ofthe present invention, and a fungicide for agricultural andhorticultural use that contains that oxime ether derivative (A) as anactive ingredient thereof.

[wherein, R₁₁ represents a hydrogen atom, C₁₋₆ alkyl group, C₁₋₆alkylcarbonyl group or C₁₋₆ alkylsulfonyl group; R₂₁ represents a C₁₋₆alkyl group or C₁₋₆ alkoxy group; R₃₁ represents a halogen atom, C₁₋₆alkyl group or C₁₋₆ alkoxy group; A represents an optionally branchedC₁₋₆ alkylene group or a bond; Q represents a phenyl group which may besubstituted with G, a group represented by formula (A1) or a grouprepresented by formula (A2); and m represents 0 or an integer of 1 to 4:

(wherein, R₄₁ represents a hydrogen atom, C₁₋₆ alkyl group, C₂₋₆ alkenylgroup or SiR₅₁R₆₁R₇₁, R₅₁ to R₇₁ each independently represent a C₁₋₆alkyl group; R₈₁ represents a hydrogen atom, C₁₋₆ alkyl group, C₁₋₆haloalkyl group, or phenyl group which may be substituted with G; Y₁represents a hydrogen atom, C₁₋₆ alkyl group, C₃₋₆ cycloalkyl group,C₃₋₆ cycloalkyl-C₁₋₆ alkyl group, C₂₋₆ alkenyl group, C₂₋₆ alkynylgroup, or phenyl C₁₋₆ alkyl group which may be substituted with G, and

G represents a halogen atom, C₁₋₆ alkyl group, C₁₋₆ alkoxy group, C₁₋₆haloalkyl group or C₁₋₆ haloalkoxy group, and these G may be the same ordifferent and substitute at 2 to 5 locations)].

-   [Patent Document 1] Japanese Unexamined Patent Application, First    Publication No. 2004-168683

DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention

Although examples of a compound related to the present invention inwhich Q is represented by formula (A2) have been cited, examples thereofhave not been described, and the biological activity of that compoundhas been unknown.

With the foregoing in view, an object of the present invention is toprovide a novel oxime ether derivative or salt thereof that can beindustrially produced advantageously and can be an active ingredient ofa fungicide for agricultural and horticultural use that demonstratesreliable effects and can be used safety, and to provide a fungicide foragricultural and horticultural use that contains at least one of thesecompounds as an active ingredient thereof.

Means for Solving the Problems

As a result of conducting extensive studies to solve the aforementionedproblems, the inventors of the present invention found that a novelcompound represented by formula (I) can actually be produced and thatsuch compounds have superior bactericidal activity, thereby leading tocompletion of the present invention. Namely, the present inventionrelates to an oxime ether derivative represented by the followingformula (I), or a salt thereof:

[wherein, X represents a halogen atom, C₁₋₂₀ alkyl group, C₁₋₂₀ alkoxygroup, C₁₋₂₀ haloalkyl group or C₁₋₂₀ haloalkoxy group,

R¹ and R² each independently represent a hydrogen atom, halogen atom,C₁₋₂₀ alkyl group, C₁₋₂₀ haloalkyl group, optionally substituted C₃₋₁₀cycloalkyl group, or R¹ and R² may bond together to form a ring,

R³ represents a hydrogen atom, C₁₋₂₀ alkyl group, C₂₋₂₀ alkenyl group,C₂₋₂₀ alkynyl group, C₁₋₂₀ haloalkyl group, C₂₋₂₀ haloalkenyl group,C₂₋₂₀ haloalkynyl group or optionally substituted C₃₋₁₀ cycloalkylgroup,

R⁴ represents a hydrogen atom, C₁₋₂₀ alkyl group, optionally substitutedC₃₋₁₀ cycloalkyl group, C₂₋₂₀ alkenyl group, C₂₋₂₀ alkynyl group, C₁₋₂₀haloalkyl group, C₂₋₂₀ haloalkenyl group, C₂₋₂₀ haloalkynyl group, cyanogroup, nitro group or optionally substituted amino group,

R⁵ represents a hydrogen atom, C₁₋₂₀ alkyl group, acyl group, formylgroup, C₁₋₂₀ alkoxy-C₁₋₂₀ alkyl group, C₂₋₂₀ acyloxy-C₁₋₂₀ alkyl group,C₁₋₂₀ alkoxycarbonyl group, C₁₋₂₀ alkylsulfonyl group or optionallysubstituted phenylsulfonyl group,

Y represents an oxygen atom or sulfur atom,

Z represents a single bond, oxygen atom, sulfur atom or NR⁶ (wherein, R⁶represents a hydrogen atom or C₁₋₃₀ alkyl group),

Het represents an optionally substituted heterocyclic group,

m represents an integer of 1 to 8, and R¹ and R² may be the same ordifferent in the case m is 2 or more, and

n represents an integer of 0 to 4, and X may be the same or different inthe case n is 2 or more].

In a second aspect thereof, the present invention relates to a fungicidefor agricultural and horticultural use that contains at least one of theoxime ether derivative of the present invention, or salt thereof, as anactive ingredient thereof.

In a third aspect thereof, the present invention relates to a ketonederivative represented by the following formula (II). This ketonederivative is a production intermediate of the oxime ether derivativerepresented by formula (I).

[wherein, X represents a halogen atom, C₁₋₂₀ alkyl group, C₁₋₂₀ alkoxygroup, C₁₋₂₀ haloalkyl group or C₁₋₂₀ haloalkoxy group,

R³ represents a hydrogen atom, C₁₋₂₀ alkyl group, C₂₋₂₀ alkenyl group,C₂₋₂₀ alkynyl group, C₁₋₂₀ haloalkyl group, C₂₋₂₀ haloalkenyl group,C₂₋₂₀ haloalkynyl group or optionally substituted C₃₋₁₀ cycloalkylgroup,

R⁴ represents a hydrogen atom, C₁₋₂₀ alkyl group, optionally substitutedC₃₋₁₀ cycloalkyl group, C₂₋₂₀ alkenyl group, C₂₋₂₀ alkynyl group, C₁₋₂₀haloalkyl group, C₂₋₂₀ haloalkenyl group, C₂₋₂₀ haloalkynyl group, cyanogroup, nitro group or optionally substituted amino group,

R⁵ represents a hydrogen atom, C₁₋₂₀ alkyl group, acyl group, formylgroup, C₁₋₂₀ alkoxy-C₁₋₂₀ alkyl group, C₂₋₂₀ acyloxy-C₁₋₂₀ alkyl group,C₁₋₂₀ alkoxycarbonyl group, C₁₋₂₀ alkylsulfonyl group or optionallysubstituted phenylsulfonyl group,

Y represents an oxygen atom or sulfur atom,

Z represents a single bond, oxygen atom, sulfur atom or NR⁶ (wherein, R⁶represents a hydrogen atom or C₁₋₃₀ alkyl group), and

n represents an integer of 0 to 4, and X may be the same or different inthe case n is 2 or more].

Effects of the Invention

The oxime ether derivative of the present invention, or salt thereof, isa novel compound, can be industrially produced advantageously, and isuseful as an active ingredient of a fungicide for agricultural andhorticultural use that has reliable effects and can be used safely.

The fungicide for agricultural and horticultural use of the presentinvention is a chemical agent that has superior control effects, doesnot cause chemical damage or contamination of plants, and has lesstoxicity to humans, animals and fish as well as little effect on theenvironment.

Furthermore, the ketone derivative of the present invention is a novelcompound, and is an important key intermediate for producing the oximeether derivative compound of the present invention.

BEST MODE FOR CARRYING OUT THE INVENTION

The following provides a detailed explanation of the present invention.

1) Oxime Ether Derivatives Represented by Formula (I) or Salt Thereof

In a first aspect thereof, the present invention is an oxime etherderivative represented by the aforementioned formula (I), or a saltthereof.

In formula (I), X represents a halogen atom, C₁₋₂₀ alkyl group, C₁₋₂₀alkoxy group, C₁₋₂₀ haloalkyl group or C₁₋₂₀ haloalkoxy group.

Examples of halogen atoms of X include a fluorine atom, chlorine atomand bromine atom.

C₁₋₂₀ alkyl groups may be linear or branched, and examples include amethyl group, ethyl group, n-propyl group, i-propyl group, n-butylgroup, i-butyl group, s-butyl group, t-butyl group, n-pentyl group,n-hexyl group, n-heptyl group, n-octyl group and n-decyl group.

C₁₋₂₀ alkoxy groups may be linear or branched, and examples include amethoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxygroup, i-butoxy group, s-butoxy group, t-butoxy group, n-pentyloxy groupand n-hexyloxy group.

There are no particular limitations on the C₁₋₂₀ haloalkyl groupsprovided they are alkyl groups substituted with a halogen atom, specificexamples of which include a fluoromethyl group, chloromethyl group,bromomethyl group, difluoromethyl group, dichloromethyl group,dibromomethyl group, trifluoromethyl group, trichloromethyl group,tribromomethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethylgroup and pentafluoroethyl group.

There are no particular limitations on the C₁₋₂₀ haloalkoxy groupsprovided they are alkoxy groups substituted with a halogen atom,specific examples of which include a chloromethoxy group,dichloromethoxy group, trichloromethoxy group, trifluoromethoxy group,1-fluoroethoxy group, 1,1-difluoroethoxy group, 2,2,2-trifluoroethoxygroup and pentafluoroethoxy group.

R¹ and R² each independently represent a hydrogen atom, halogen atom,C₁₋₂₀ alkyl group, C₁₋₂₀ haloalkyl group or optionally substituted C₃₋₁₀cycloalkyl group.

Specific examples of halogen atoms, C₁₋₂₀ alkyl groups and C₁₋₂₀haloalkyl groups of R¹ and R² are the same as those listed as specificexamples of the halogen atoms, C₁₋₂₀ alkyl groups and C₁₋₂₀ haloalkylgroups of X.

Examples of C₃₋₁₀ cycloalkyl groups of optionally substituted C₃₋₁₀cycloalkyl groups of R¹ and R² include a cyclopropyl group, cyclobutylgroup, cyclopentyl group, cyclohexyl group, cycloheptyl group andcyclooctyl group.

Examples of substituents of the C₃₋₁₀ cycloalkyl groups include ahalogen atom such as a fluorine atom, chlorine atom or bromine atom;C₁₋₆ alkyl group such as a methyl group or ethyl group; C₁₋₆ alkoxygroup such as a methoxy group or ethoxy group; nitro group; and, cyanogroup.

In addition, R¹ and R² may bond together to form a ring, and aheteroatom such as an oxygen atom, sulfur atom or nitrogen atom may becontained in the ring. Examples of such rings include a cyclopropanering, cyclopentane ring, cyclohexane ring and tetrahydropyran ring.

R³ represents a hydrogen atom, C₁₋₂₀ alkyl group, C₂₋₂₀ alkenyl group,C₂₋₂₀ alkynyl group, C₁₋₂₀ haloalkyl group, C₂₋₂₀ haloalkenyl group,C₂₋₂₀ haloalkynyl group and optionally substituted C₃₋₁₀ cycloalkylgroup.

Specific examples of C₁₋₂₀ alkyl groups, C₁₋₂₀ haloalkyl groups andoptionally substituted C₃₋₁₀ cycloalkyl groups of R³ are the same asthose listed as specific examples of C₁₋₂₀ alkyl groups, C₁₋₂₀ haloalkylgroups and optionally substituted C₃₋₁₀ cycloalkyl groups of X, R¹ andR².

Examples of C₂₋₂₀ alkenyl groups of R³ include a vinyl group, 1-propenylgroup, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenylgroup, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenylgroup, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group,1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group,2-hexenyl group, 3-hexenyl group, 4-hexenyl group and 5-hexenyl group.

Examples of C₂₋₂₀ alkynyl groups include an ethynyl group, 1-propynylgroup, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynylgroup, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynylgroup, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group,1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group and1,1-dimethyl-2-butynyl group.

Examples of C₂₋₂₀ haloalkenyl groups include a 3-chloro-2-propenylgroup, 4-chloro-2-butenyl group, 4,4-dichloro-3-butenyl group,4,4-difluoro-3-butenyl group and 3,3-dichloro-2-propenyl group.

Examples of C₂₋₂₀ haloalkynyl groups include a 3-chloro-1-propynylgroup, 3-chloro-1-butynyl group, 3-bromo-1-butynyl group,3-bromo-2-propynyl group and 3-iodo-2-propynyl group.

R⁴ represents a hydrogen atom, C₁₋₂₀ alkyl group, optionally substitutedC₃₋₁₀ cycloalkyl group, C₂₋₂₀ alkenyl group, C₂₋₂₀ alkynyl group, C₁₋₂₀haloalkyl group, C₂₋₂₀ haloalkenyl group, C₂₋₂₀ haloalkynyl group, cyanogroup, nitro group or optionally substituted amino group.

Specific examples of C₁₋₂₀ alkyl groups of R⁴ are the same as thoselisted as specific examples of C₁₋₂₀ alkyl groups of X.

Specific examples of optionally substituted C₃₋₁₀ cycloalkyl groups ofR⁴ are the same as those listed as specific examples of optionallysubstituted C₃₋₁₀ cycloalkyl groups of R¹.

Specific examples of C₂₋₂₀ alkenyl groups, C₂₋₂₀ alkynyl groups, C₁₋₂₀haloalkyl groups, C₂₋₂₀ haloalkenyl groups and C₂₋₂₀ haloalkynyl groupsof R⁴ are the same as those listed as specific examples of C₂₋₂₀ alkenylgroups, C₂₋₂₀ alkynyl groups, C₁₋₂₀ haloalkyl groups, C₂₋₂₀ haloalkenylgroups and C₂₋₂₀ haloalkynyl groups of R³.

Examples of optionally substituted amino groups of R⁴ include an aminogroup; mono (C₁₋₆) alkylamino groups such as a methylamino group,ethylamino group or i-propylamino group; di(C₁₋₆) alkylamino groups suchas a dimethylamino group or diethylamino group; acylamino groups such asan acetylamino group or benzoylamino group; and, optionally substitutedphenylamino groups such as a phenylamino group or 4-methylphenylaminogroup.

R⁵ represents a hydrogen atom, C₁₋₂₀ alkyl group, acyl group, formylgroup, C₁₋₂₀ alkoxy-C₁₋₂₀ alkyl group, C₂₋₂₀ acyloxy-C₁₋₂₀ alkyl group,C₁₋₂₀ alkoxycarbonyl group, C₁₋₂₀ alkylsulfonyl group or optionallysubstituted phenylsulfonyl group.

Specific examples of C₁₋₂₀ alkyl groups of R⁵ are the same as thoselisted as specific examples of C₁₋₂₀ alkyl groups of X.

Examples of acyl groups include an acetyl group, propionyl group,pivaloyl group, trifluoroacetyl group, trichloroacetyl group, benzoylgroup, 4-methylbenzoyl group and 2-chlorobenzoyl group.

Examples of C₁₋₂₀ alkoxy-C₁₋₂₀ alkyl groups of R⁵ include amethoxymethyl group, ethoxymethyl group, i-propoxymethyl group,1-methoxyethyl group, 2-methoxyethyl group, 1-ethoxyethyl group,2-ethoxyethyl group, 1-methoxy-n-propyl group, 2-methoxy-n-propyl groupand 3-methoxy-n-propyl group.

Examples of C₂₋₂₀ acyloxy-C₁₋₂₀ alkyl groups of R⁵ include anacetoxymethyl group, acetoxyethyl group, propionyloxymethyl group,pivaloyloxymethyl group, 1-acetoxyethyl group, 2-acetoxyethyl group and1-acetoxy-n-propyl group.

Examples of C₁₋₂₀ alkoxycarbonyl groups of R⁵ include a methoxycarbonylgroup, ethoxycarbonyl group, isopropoxycarbonyl group, n-butoxycarbonylgroup and t-butoxycarbonyl group.

Examples of C₁₋₂₀ alkylsulfonyl groups include a methylsulfonyl group,ethylsulfonyl group, n-propylsulfonyl group and i-propylsulfonyl group.

Examples of optionally substituted phenylsulfonyl groups include aphenylsulfonyl group, 4-methylphenylsulfonyl group,2-chlorophenylsulfonyl group and 2,4-dimethylphenylsulfonyl group.

Y represents an oxygen atom or sulfur atom.

Z represents a single bond, oxygen atom, sulfur atom or grouprepresented by NR⁶.

R⁶ represents a hydrogen atom or a C₁₋₃₀ alkyl group such as methylgroup, ethyl group, n-propyl group, i-propyl group, n-butyl group ort-butyl group.

Het represents an optionally substituted heterocyclic group. Theheterocyclic group is a saturated or unsaturated heterocyclic groupcontaining 1 to 4 N, O or S atoms in the ring thereof, and is preferablya 5-member or 6-member heterocyclic group.

Specific examples of heterocyclic groups include unsaturated 5-memberheterocyclic groups such as a furan-2-yl group, furan-3-yl group,thiophen-2-yl group, thiophen-3-yl group, pyrrol-2-yl group, pyrrol-3-ylgroup, oxazol-2-yl group, oxazol-4-yl group, oxazol-5-yl group,thiazol-2-yl group, thiazol-4-yl group, thiazol-5-yl group,isoxazol-3-yl group, isoxazol-4-yl group, isoxazol-5-yl group,isothiazol-3-yl group, isothiazol-4-yl group, isothiazol-5-yl group,imidazol-2-yl group, imidazol-4-yl group, imidazol-5-yl group,pyrazol-3-yl group, pyrazol-4-yl group, pyrazol-5-yl group,1,3,4-oxadiazol-2-yl group, 1,3,4-thiadiazol-2-yl group,1,2,3-triazol-4-yl group, 1,2,4-triazol-3-yl group or 1,2,4-triazol-5-ylgroup; unsaturated 6-member heterocyclic groups such as a pyridin-2-ylgroup, pyridin-3-yl group, pyridin-4-yl group, 5-chloro-3-pyridyl group,3-trifluoromethyl-2-pyridyl group, pyridazin-3-yl group, pyridazin-4-ylgroup, pyrazin-2-yl group, pyrimidin-5-yl group, 1,3,5-triazin-2-ylgroup or 1,2,4-triazin-3-yl group; and saturated or partiallyunsaturated heterocyclic groups such as a tetrahydrofuran-2-yl group,tetrahydropyran-4-yl group, piperidin-3-yl group, pyrrolidin-2-yl group,morpholino group, piperidino group, piperazino group, N-methylpiperazinogroup, aziridino group, azetidino group, pyrrolidino group, oroxazolin-2-yl group.

Examples of substituents of the above-mentioned heterocyclic groupsinclude halogen atoms such as a fluorine atom, chlorine atom or bromineatom; C₁₋₆ alkyl groups such as a methyl group, ethyl group, n-propylgroup, i-propyl group, n-butyl group, s-butyl group, i-butyl group ort-butyl group; C₁₋₆ alkoxy groups such as a methoxy group, ethoxy group,propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxygroup or t-butoxy group; C₁₋₆ haloalkoxy groups such as a chloromethoxygroup or trifluoromethoxy group; C₁₋₆ alkylthio groups such as amethylthio group, ethylthio group, n-propylthio group, i-propylthiogroup, n-butylthio group, i-butylthio group, s-butylthio group ort-butylthio group; C₁₋₆ alkylsulfonyl groups such as a methylsulfonylgroup, ethylsulfonyl group, i-propylsulfonyl group or n-butylsulfonylgroup; C₁₋₆ haloalkyl groups such as a chloromethyl group, fluoromethylgroup or trifluoromethyl group; and, C₁₋₆ alkylsulfonyloxy groups suchas a methylsulfonyloxy group, ethylsulfonyloxy group,i-propylsulfonyloxy group or n-butylsulfonyloxy group.

m represents an integer of 1 to 8 and is preferably an integer of 1 to3.

n represents an integer of 0 to 4 and is preferably an integer of 0 to2.

In the present invention, an oxime ether derivative represented by theaforementioned formula (I) is preferably a compound represented by thefollowing formula (I-1):

(wherein, R¹ to R⁵, X, Y, Z, Het, m and n are the same as previouslydefined), and more preferably a compound represented by the followingformula (I-1a):

(wherein, R¹ to R⁵, X, Z, Het, m and n are the same as previouslydefined).

(Production Method)

An oxime ether derivative compound of the present invention can beproduced, for example, in the manner described below:

(wherein, R¹ to R⁵, X, Z, Het, Y, m and n are the same as previouslydefined).

Namely, a compound represented by formula (I) can be obtained byreacting an oxyamine compound represented by formula (3) with a ketonecompound represented by formula (II) (to also be referred to as“compound (II)”).

Furthermore, compound (II) is a novel compound that is an important keyintermediate in the production of a compound represented by formula (I)of the present invention. A third aspect of the present invention is aketone derivative represented by this compound (II).

The amount of the compound (II) used is normally 0.5 to 2 times molesand preferably 0.7 to 1.5 times moles the oxyamine compound representedby formula (3).

Although the reaction can also be carried out in the absence of acatalyst, it is preferably carried out in the presence of an acidcatalyst or basic catalyst, and is more preferably carried out in thepresence of an acid catalyst.

Examples of acid catalysts used include trifluoroacetic acid,benzenesulfonic acid, p-toluenesulfonic acid, p-toluenesulfonic acidmonohydrate, methanesulfonic acid, pyridinium p-toluenesulfonate,hydrochloric acid and sulfuric acid. Examples of basic catalysts includepyridine, triethylamine and potassium hydroxide.

The amount of catalyst used is normally 0.0001 to 1 times moles theoxyamine compound represented by formula (3).

In addition, a dehydrating agent such as anhydrous sodium sulfate ormolecular sieve may also be added to the reaction system.

The reaction can be carried out in a suitable solvent. There are noparticular limitations on the solvent used provided it is inert in thereaction. Examples of solvents include ether-based solvents such asdioxane, 1,2-dimethoxyethane or tetrahydrofuran; aromatichydrocarbon-based solvents such as toluene, benzene or xylene; aliphatichydrocarbon-based solvents such as n-pentane, n-hexane or n-heptane;halogenated hydrocarbon-based solvents such as dichloromethane,chloroform, carbon tetrachloride or 1,2-dichloroethane; amide-basedsolvents such as N,N-dimethylformamide, N,N-dimethylacetamide orN-methylpyrrolidone; nitrile-based solvents such as acetonitrile orbenzonitrile; alcohol-based solvents such as methanol, ethanol orn-propanol; and mixed solvents composed of two more of these solvents.

Although there are no particular limitations on the amount of solventused, it is normally 1 to 100 ml based on 1 g of the oxyamine compoundrepresented by formula (3).

The reaction temperature is within a temperature range from roomtemperature to the boiling point of the solvent used. The reaction timeis normally from several minutes to several tens of hours.

The oxyamine compound represented by formula (3) can be produced by aconventionally known method for producing oxyamine compounds. Forexample, as indicated below, an oxyamine compound represented by formula(3) can be obtained by reacting carbon tetrabromide andtriphenylphosphine with a compound represented by formula (1) to obtaina compound represented by formula (2), reactingN-t-butoxycarbonylhydroxylamine therewith in the presence of base toobtain an oxyamine compound represented by formula (9), and allowing anacid to act thereon:

(wherein, R¹, R², Het and m are the same as previously defined).

In addition, in the case of reacting an oxyamine compound represented byformula (3) with compound (4), the reaction may be carried out by mixingcompound (II) with an oxyamine compound represented by formula (9)followed by adding an acid such as trifluoroacetic acid to form acompound represented by formula (3) within the reaction system.

Compound (II) can be produced, for example, in the manner indicatedbelow:

(wherein, X, n, R³ to R⁵, Y and Z are the same as previously defined).

Namely, a hydroxycarbamic acid compound represented by formula (7) (toalso be referred to as “compound (7)”) is obtained by reacting acompound represented by formula (6) (to also be referred to as “compound(6)”) with a fluoride compound represented by formula (5) (to also bereferred to as “compound (5)”) in the presence of base. Next, the targetcompound (II) is obtained by reacting an amide compound represented byformula (8) (to also be referred to as “compound (8)”) with compound (7)in the presence of base.

In the reaction for obtaining compound (7), the amount of compound (6)used is normally 0.8 to 5 times moles and preferably 1 to 3 times molesbased on 1 mole of compound (5).

Examples of base used in the reaction for obtaining compound (7) includemetal hydroxides such as lithium hydroxide, sodium hydroxide, potassiumhydroxide, magnesium hydroxide or calcium hydroxide; metal alkoxidessuch as sodium methoxide, sodium ethoxide, potassium methoxide,potassium ethoxide or potassium t-butoxide; metal hydrides such assodium hydride, potassium hydride or calcium hydride; and organic basessuch as triethylamine, diisopropylethylamine, pyridine,1,8-diazabicylo[5.4.0]undec-7-ene (DBU) or 1,4-diazabicylo[2.2.2]octane.

The amount of base used is normally 1 to 20 times moles based on 1 moleof compound (5).

This reaction can be carried out in a suitable organic solvent. Thereare no particular limitations on the organic solvent used provided it isinert in the reaction. Examples of organic solvents includesulfur-containing solvents such as dimethylsulfoxide ordiethylsulfoxide; ether-based solvents such as dioxane,1,2-dimethoxyethane or tetrahydrofuran; aromatic hydrocarbon-basedsolvents such as toluene, benzene or xylene; aliphatic hydrocarbon-basedsolvents such as n-pentane, n-hexane or n-heptane; amide-based solventssuch as N,N-dimethylformamide, N,N-dimethylacetamide orN-methylpyrrolidone; nitrile-based solvents such as acetonitrile orbenzonitrile; and mixed solvents composed of two or more of thesesolvents.

Although there are no particular limitations on the amount of organicsolvent used, it is normally 1 to 100 ml based on 1 g of compound (5).

The reaction for obtaining compound (7) proceeds smoothly within atemperature range from 0° C. to the boiling point of the solvent.

Specific examples of compound (8) used in the reaction for obtainingcompound (II) include N,N-dimethylacetamide andN,N-dimethylpropionamide.

The amount of compound (8) used is normally 0.8 to 5 times moles andpreferably 1 to 3 times moles based on 1 mole of compound (7).

Examples of base used in the reaction for obtaining compound (II)include organic lithium compounds such as n-butyllithium,sec-butyllithium, t-butyllithium or lithium diisopropylamide; alkalinemetals such as sodium metal or potassium metal; and metal hydrides suchas sodium hydride, potassium hydride or calcium hydride.

The amount of base used is normally 1 to 20 times moles based on 1 moleof compound (7).

This reaction can be carried out in a suitable organic solvent. Thereare no particular limitations on the solvent used provided it is inertin the reaction. Examples of organic solvents include ether-basedsolvents such as dioxane, 1,2-dimethoxyethane or tetrahydrofuran;aromatic hydrocarbon-based solvents such as toluene, benzene or xylene;and aliphatic hydrocarbon-based solvents such as n-pentane, n-hexane orn-heptane.

The reaction for obtaining compound (II) proceeds smoothly within atemperature range from −100° C. to the boiling point of the solventused.

Among compounds represented by formula (II), a compound (II-a), in whichR³ is a t-butyl group, R⁵ is a hydrogen atom and Y and Z are oxygenatoms, can be derived to a compound (II-c), in which the t-butyl groupis replaced with another substituent R³′ (wherein, R³′ is the same asthe previously defined R³ except for a t-butyl group) according to aknown method as indicated below:

(wherein, X, n, R⁴ are the same as previously defined, and Halrepresents a halogen atom such as a chlorine atom or bromine atom).

Namely, a compound represented by formula (II-b) is first obtained byreacting a halogenoxy acid ester compound represented by formula (9)with a carbamic acid t-butyl ester compound represented by formula(II-a) in the presence of base. Next, a compound represented by formula(II-c) can be obtained by allowing an acid to act thereon.

Examples of base used in the reaction for reacting the halogenoxy acidester compound represented by formula (9) include metal hydroxides suchas lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesiumhydroxide or calcium hydroxide; metal alkoxides such as sodiummethoxide, sodium ethoxide, potassium methoxide, potassium ethoxide orpotassium t-butoxide; metal hydrides such as sodium hydride, potassiumhydride or calcium hydride; and organic bases such as triethylamine,diisopropylethylamine, pyridine, 1,8-diazabicylo[5.4.0]undec-7-ene (DBU)or 1,4-diazabicylo[2.2.2]octane.

The amount of base used is normally 1 to 20 times moles based on 1 moleof compound (II-a).

The reaction for reacting the halogenoxy acid ester compound representedby formula (9) is carried out in a suitable organic solvent. There areno particular limitations on the organic solvent used provided it isinert in the reaction. Examples of organic solvents include halogenatedhydrocarbons such as methylene chloride, chloroform, carbontetrachloride or 1,2-dichloroethane; sulfur-containing solvents such asdimethylsulfoxide or diethylsulfoxide; ether-based solvents such asdioxane, 1,2-dimethoxyethane or tetrahydrofuran; aromatichydrocarbon-based solvents such as toluene, benzene or xylene; aliphatichydrocarbon-based solvents such as n-pentane, n-hexane or n-heptane;amide-based solvents such as N,N-dimethylformamide,N,N-dimethylacetamide or N-methylpyrrolidone; nitrile-based solventssuch as acetonitrile or benzonitrile; and mixed solvents composed of twoor more of these solvents.

Although there are no particular limitations on the amount of organicsolvent used, it is normally 1 to 100 ml based on 1 g of compound(II-b).

The reaction for reacting the halogenoxy acid ester compound representedby formula (9) proceeds smoothly within a temperature range from −20° C.to the boiling point of the solvent used.

Although varying according to the reaction scale, the reaction time isnormally from several minutes to several tens of hours.

Examples of acids used in the reaction for obtaining a compoundrepresented by formula (II-c) from a compound represented by formula(II-b) include inorganic acids such as hydrochloric acid, sulfuric acidor nitric acid; acetic acid, trifluoroacetic acid, methanesulfonic acidand p-toluenesulfonic acid.

The amount of acid used is normally 1 to 20 times moles based on 1 moleof compound (II-b).

The reaction for obtaining a compound represented by formula (II-c) froma compound represented by formula (II-b) is carried out in a suitableorganic solvent.

There are no particular limitations on the organic solvent used providedit is inert in the reaction, and examples of organic solvents usedinclude the same organic solvents listed as examples of solvents able tobe used in the reaction for reacting the halogenoxy acid ester compoundrepresented by formula (9).

The reaction for obtaining a compound represented by formula (II-c) froma compound represented by formula (II-b) proceeds smoothly within atemperature range from −20° C. to the boiling point of the solvent used.

Although varying according to the reaction scale, the reaction time isnormally from several minutes to several tens of hours.

In addition, among compounds represented by formula (II), compound(II-d), in which Y and Z are oxygen atoms, can be derived to compound(II-e), in which substituent R³ is converted to another substituent R³″,by a known transesterification method (as indicated by the followingreaction formula):

(wherein, X, n and R³ to R⁵ are the same as previously defined, and R³″is defined in the same manner as R³, provided that R³ and R³″ are notthe same).

There are no particular limitations on salts of the oxime etherderivative compound of the present invention provided it is anagriculturally and horticulturally acceptable salt. Examples of saltsinclude salts of inorganic acids such as hydrochlorides or sulfates; andsalts of organic acids such as acetates or lactates.

These salts can be produced in accordance with conventionally knownmethods using an oxime ether derivative represented by theaforementioned formula (I) and a corresponding acid.

In any of the reactions, a target compound can be isolated by carryingout an ordinary post-treatment procedure following completion of thereaction and purifying by known, commonly used purification means suchas distillation, recrystallization or column chromatography as desired.

The structure of a target compound can be identified and confirmed byknown analysis means such as IR spectroscopy, NMR spectroscopy, massspectrometry or elementary analysis.

Although geometrical isomers (cis and trans isomers) based oncarbon-nitrogen double bonds exist for the oxime ether derivative of thepresent invention, all of these isomers are included in the presentinvention.

Examples of the oxime ether derivative of the present invention obtainedin the manner described above are shown in the following first tables(Tables 1 to 33). In the first tables, although only one of thegeometrical isomers of the oxime ether derivatives are shown, the othergeometrical isomer can be similarly exemplified.

In the following chemical formulas, r represents a C₁₋₆ alkyl group suchas a methyl group or ethyl group; C₁₋₆ haloalkyl group such as atrifluoromethyl group; C₁₋₆ alkoxy group such as a methoxy group orethoxy group; C₁₋₆ haloalkoxy group such as a trifluoromethoxy group; orhalogen atom such as a fluorine atom, chlorine atom or bromine atom. t1represents an integer of 0 to 2, t2 represents an integer of 0 to 3, andt3 represents an integer of 0 to 4. In the case t1 is 2 or in the caset2 or t3 is 2 or more, r may be the same or different.

In addition, in the following first tables, Et represents an ethylgroup, Ph a phenyl group, c-Pr a cyclopropyl group, and di indicatesdi-substitution, while an asterisk (*) indicates the location of a bond.In addition, in the tables, numbers indicated in the r and X columnsrepresent their respective substituted locations.

In addition, only one of the stereoisomers in a C═N double bond isassumed to not be represented.

(First Tables)

TABLE 1 (I-1)

No Het r R¹ R² m R⁴ R⁵ X n Y Z R³ 1 A1 — H H 1 CH₃ H — 0 O O CH₃ 2 A1 —H H 1 CH₃ H 2-Cl 1 O O CH₃ 3 A1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 4 A14-Et H H 1 CH₃ H 2-C1 1 O O CH₃ 5 A1 4-CF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 6A1 4-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 7 A1 4-Cl H H 1 CH₃ H 2-Cl 1 O O CH₃ 8A1 4-OCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 9 A1 4-OEt H H 1 CH₃ H 2-Cl 1 O OCH₃ 10 A1 4-OCF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 11 A1 5-CH₃ H H 1 CH₃ H 2-Cl1 O O CH₃ 12 A1 5-Et H H 1 CH₃ H 2-Cl 1 O O CH₃ 13 A1 5-CF₃ H H 1 CH₃ H2-Cl 1 O O CH₃ 14 A1 5-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 15 A1 5-Cl H H 1 CH₃H 2-Cl 1 O O CH₃ 16 A1 5-OCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 17 A1 5-OEt H H1 CH₃ H 2-Cl 1 O O CH₃ 18 A1 5-OCF₃ H H I CH₃ H 2-Cl 1 O O CH₃ 19 A14,5-diCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 20 A1 4-Et-5-OH₃ H H 1 CH₃ H 2-Cl 1O O CH₃ 21 A1 4-CF₃-5-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 22 A1 4,5-diF H H 1CH₃ H 2-Cl 1 O O CH₃ 23 A1 4-Cl-5-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 24 A14,5-diOCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 25 A1 4-OEt-5-CH₃ H H 1 CH₃ H 2-Cl1 O O CH₃ 26 A1 4-OCF₃-5-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 27 A1 4-CH₃ H CH₃1 CH₃ H 2-C1 1 O O CH₃ 28 A1 4-Et H CH₃ 1 CH₃ H 2-Cl 1 O O CH₃ 29 A14-CH₃ H Et 1 CH₃ H 2-Cl 1 O O CH₃ 30 A1 4-CH₃ H i-Pr 1 CH₃ H 2-Cl 1 O OCH₃ 31 A1 4-CH₃ CH₃ Et 1 CH₃ H 2-Cl 1 O O CH₃ 32 A1 4-CH₃ H F 1 CH₃ H2-Cl 1 O O CH₃ 33 A1 4-CH₃ F F 1 CH₃ H 2-Cl 1 O O CH₃ 34 A1 4-CH₃ H CF31 CH₃ H 2-Cl 1 O O CH₃ 35 A1 4-CH₃ H c-Pr 1 CH₃ H 2-Cl 1 O O CH₃ 36 A14-CH₃ —CH₂CH₂— 1 CH₃ H 2-Cl 1 O O CH₃ 37 A1 4-CH₃ —CH₂CH₂CH₂— 1 CH₃ H2-Cl 1 O O CH₃ 38 A1 4-CH₃ —CH₂CH(CH₃)— 1 CH₃ H 2-Cl 1 O O CH₃ 39 A14-CH₃ —CH₂C(CH₃)2— 1 CH₃ H 2-C1 1 O O CH₃ 40 A1 4-CH₃ H H 1 H H 2-Cl 1 OO CH₃ 41 A1 4-CH₃ H H 1 Et H 2-Cl 1 O O CH₃ 42 A1 4-CH₃ H H 1 c-Pr H2-C1 1 O O CH₃ 43 A1 4-CH₃ H H 1 CH═CH₂ H 2-Cl 1 O O CH₃ 44 A1 4-CH₃ H H1 CH₂CH═CH₂ H 2-Cl 1 O O CH₃ 45 A1 4-CH₃ H H 1 ethynyl H 2-Cl 1 O O CH₃46 A1 4-CH₃ H H 1 Propargyl H 2-Cl 1 O O CH₃ 47 A1 4-CH₃ H H 1 CF₃ H2-C1 1 O O CH₃ 48 A1 4-CH₃ H H 1 CH═CHCl H 2-C1 1 O O CH₃ 49 A1 4-CH₃ HH 1 3,3,2-tri-lodo-allyl H 2-Cl 1 O O CH₃ 50 A1 4-CH₃ H H 13-Iodopropargyl H 2-Cl 1 O O CH₃ 51 A1 4-CH₃ H H 1 CN H 2-Cl 1 O O CH₃52 A1 4-CF₃ H H 1 CN H 2-Cl 1 O O CH₃

TABLE 2 53 A1 4-CH₃ H H 1 NO₂ H 2-Cl 1 O O CH₃ 54 A1 4-CH₃ H H 1 NH₂ H2-Cl 1 O O CH₃ 55 A1 4-CH₃ H H 1 NHCH₃ H 2-Cl 1 O O CH₃ 56 A1 4-CH₃ H H1 N(CH₃)₂ H 2-Cl 1 O O CH₃ 57 A1 4-CH₃ H H 1 CH₃ CH₃ 2-Cl 1 O O CH₃ 58A1 4-CH₃ H H 1 CH₃ Et 2-Cl 1 O O CH₃ 59 A1 4-CH₃ H H 1 CH₃ CH₃CO 2-Cl 1O O CH₃ 60 A1 4-CH₃ H H 1 CH₃ CH₃CH₂CO 2-Cl 1 O O CH₃ 61 A1 4-CH₃ H H 1CH₃ PhCO 2-Cl 1 O O CH₃ 62 A1 4-CH₃ H H 1 CH₃ 4-Cl-PhCO 2-Cl 1 O O CH₃63 A1 4-CH₃ H H 1 CH₃ PhCH₂CO 2-Cl 1 O O CH₃ 64 A1 4-CH₃ H H 1 CH₃ CHO2-Cl 1 O O CH₃ 65 A1 4-CH₃ H H 1 CH₃ CH₃OCH₂ 2-Cl 1 O O CH₃ 66 A1 4-CH₃H H 1 CH₃ CH₃CH(OCH₃) 2-Cl 1 O O CH₃ 67 A1 4-CH₃ H H 1 CH₃ CH₃SO₂ 2-Cl 1O O CH₃ 68 A1 4-CH₃ H H 1 CH₃ PhSO₂ 2-Cl 1 O O CH₃ 69 A1 4-CH₃ H H 1 CH₃4-CH₃-PhSO₂ 2-Cl 1 O O CH₃ 70 A1 4-CH₃ H H 1 CH₃ H 2-Cl 1 S O CH₃ 71 A14-CH₃ H H 1 CH₃ H 2-Cl 1 O S CH₃ 72 A1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O — CH₃73 A1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O NH CH₃ 74 A1 4-CH₃ H H 1 CH₃ H 2-Cl 1 ONCH₃ CH₃ 75 A1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O H 76 A1 4-CH₃ H H 1 CH₃ H2-Cl 1 O O Et 77 A1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O n-Pr 78 A1 4-CH₃ H H 1CH₃ H 2-Cl 1 O O CH₂CH═CH₂ 79 A1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH═CH₂ 80A1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O Propargyl 81 A1 4-CH₃ H H 1 CH₃ H 2-Cl 1O O ethynyl 82 A1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O CF₃ 83 A1 4-CH₃ H H 1 CH₃H 2-Cl 1 O O CH₂CF₃ 84 A1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O CF₂CF₃ 85 A14-CH₃ H H 1 CH₃ H 2-Cl 1 O O CF₂CF₂H 86 A1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O OCH₂CH═CHCl 87 A1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O 3-Iodo-propargyl 88 A14-CH₃ H H 1 CH₃ H 2-Cl 1 O O c-Pr 89 A1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O Oc-Hex 90 A1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O 2-CH₃-c-Pr 91 A1 — H H 1 CH₃ H2-CH₃ 1 O O CH₃ 92 A1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 93 A1 4-Et H H 1CH₃ H 2-CH₃ 1 O O CH₃ 94 A1 4-CF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 95 A1 4-FH H 1 CH₃ H 2-CH₃ 1 O O CH₃ 96 A1 4-Cl H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 97 A14-OCH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 98 A1 4-OEt H H 1 CH₃ H 2-CH₃ 1 O OCH₃ 99 A1 4-OCF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 100 A1 5-CH₃ H H 1 CH₃ H2-CH₃ 1 O O CH₃ 101 A1 5-Et H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 102 A1 5-CF₃ H H1 CH₃ H 2-CH₃ 1 O O CH₃ 103 A1 5-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 104 A15-Cl H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 105 A1 5-OCH₃ H H 1 CH₃ H 2-CH₃ 1 O OCH₃ 106 A1 5-OEt H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 107 A1 5-OCF₃ H H 1 CH₃ H2-CH₃ 1 O O CH₃ 108 A1 4,5-diCH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 109 A14-Et-5-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 110 A1 4-CF₃-5-F H H 1 CH₃ H2-CH₃ 1 O O CH₃ 111 A1 4,5-diF H H 1 CH₃ H 2-CH₃ 1 O O CH₃

TABLE 3 112 A1 4-Cl-5-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 113 A1 4,5-diOCH₃ HH 1 CH₃ H 2-CH₃ 1 O O CH₃ 114 A1 4-OEt-5-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃115 A1 4-OCF₃-5-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 116 A1 4-CH₃ H CH₃ 1 CH₃ H2-CH₃ 1 O O CH₃ 117 A1 4-Et H CH₃ 1 CH₃ H 2-CH₃ 1 O O CH₃ 118 A1 4-CH₃ HEt 1 CH₃ H 2-CH₃ 1 O O CH₃ 119 A1 4-CH₃ H i-Pr 1 CH₃ H 2-CH₃ 1 O O CH₃120 A1 4-CH₃ CH₃ Et 1 CH₃ H 2-CH₃ 1 O O CH₃ 121 A1 4-CH₃ H F 1 CH₃ H2-CH₃ 1 O O CH₃ 122 A1 4-CH₃ F F 1 CH₃ H 2-CH₃ 1 O O CH₃ 123 A1 4-CH₃ HCF₃ 1 CH₃ H 2-CH₃ 1 O O CH₃ 124 A1 4-CH₃ H c-Pr 1 CH₃ H 2-CH₃ 1 O O CH₃125 A1 4-CH₃ —CH2CH2— 1 CH₃ H 2-CH₃ 1 O O CH₃ 126 A1 4-CH₃ —CH2CH2CH2— 1CH₃ H 2-CH₃ 1 O O CH₃ 127 A1 4-CH₃ —CH2CH(CH3)— 1 CH₃ H 2-CH₃ 1 O O CH₃128 A1 4-CH₃ —CH2C(CH3)2— 1 CH₃ H 2-CH₃ 1 O O CH₃ 129 A1 4-CH₃ H H 1 H H2-CH₃ 1 O O CH₃ 130 A1 4-CH₃ H H 1 Et H 2-CH₃ 1 O O CH₃ 131 A1 4-CH₃ H H1 c-Pr H 2-CH₃ 1 O O CH₃ 132 A1 4-CH₃ H H 1 CH═CH₂ H 2-CH₃ 1 O O CH₃ 133A1 4-CH₃ H H 1 CH₂CH═CH₂ H 2-CH₃ 1 O O CH₃ 134 A1 4-CH₃ H H 1 ethynyl H2-CH₃ 1 O O CH₃ 135 A1 4-CH₃ H H 1 Propargyl H 2-CH₃ 1 O O CH₃ 136 A14-CH₃ H H 1 CF₃ H 2-CH₃ 1 O O CH₃ 137 A1 4-CH₃ H H 1 CH═CHCl H 2-CH₃ 1 OO CH₃ 138 A1 4-CH₃ H H 1 3,3,2-tri-Iodo-allyl H 2-CH₃ 1 O O CH₃ 139 A14-CH₃ H H 1 3-Iodopropargyl H 2-CH₃ 1 O O CH₃ 140 A1 4-CH₃ H H 1 CN H2-CH₃ 1 O O CH₃ 141 A1 4-CF₃ H H 1 CN H 2-CH₃ 1 O O CH₃ 142 A1 4-CH₃ H H1 NO₂ H 2-CH₃ 1 O O CH₃ 143 A1 4-CH₃ H H 1 NH₂ H 2-CH₃ 1 O O CH₃ 144 A14-CH₃ H H 1 NHOH₃ H 2-CH₃ 1 O O CH₃ 145 A1 4-CH₃ H H 1 N(CH₃)₂ H 2-CH₃ 1O O CH₃ 146 A1 4-CH₃ H H 1 CH₃ CH₃ 2-CH₃ 1 O O CH₃ 147 A1 4-CH₃ H H 1CH₃ Et 2-CH₃ 1 O O CH₃ 148 A1 4-CH₃ H H 1 CH₃ CH₃CO 2-CH₃ 1 O O CH₃ 149A1 4-CH₃ H H 1 CH₃ CH₃CH₂CO 2-CH₃ 1 O O CH₃ 150 A1 4-CH₃ H H 1 CH₃ PhCO2-CH₃ 1 O O CH₃ 151 A1 4-CH₃ H H 1 CH₃ 4-Cl—PhCO 2-CH₃ 1 O O CH₃ 152 A14-CH₃ H H 1 CH₃ PhCH₂CO 2-CH₃ 1 O O CH₃ 153 A1 4-CH₃ H H 1 CH₃ CHO 2-CH₃1 O O CH₃ 154 A1 4-CH₃ H H 1 CH₃ CH₃OCH₂ 2-CH₃ 1 O O CH₃ 155 A1 4-CH₃ HH 1 CH₃ CH₃CH(OCH₃) 2-CH₃ 1 O O CH₃ 156 A1 4-CH₃ H H 1 CH₃ CH₃SO₂ 2-CH₃1 O O CH₃ 157 A1 4-CH₃ H H 1 CH₃ PhSO₂ 2-CH₃ 1 O O CH₃ 158 A1 4-CH₃ H H1 CH₃ 4-CH₃—PhSO₂ 2-CH₃ 1 O O CH₃ 159 A1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 S OCH₃ 160 A1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O S CH₃ 161 A1 4-CH₃ H H 1 CH₃ H2-CH₃ 1 O — CH₃ 162 A1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O NH CH₃ 163 A1 4-CH₃ HH 1 CH₃ H 2-CH₃ 1 O NCH₃ CH₃ 164 A1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O H 165A1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O Et 166 A1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O On-Pr 167 A1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CH═CH₂ 168 A1 4-CH₃ H H 1CH₃ H 2-CH₃ 1 O O CH═CH₂ 169 A1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O Propargyl170 A1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O ethynyl 171 A1 4-CH₃ H H 1 CH₃ H2-CH₃ 1 O O CF₃ 172 A1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CF₃ 173 A1 4-CH₃H H 1 CH₃ H 2-CH₃ 1 O O CF₂CF₃

TABLE 4 174 A1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CF₂CF₂H 175 A1 4-CH₃ H H 1CH₃ H 2-CH₃ 1 O O CH₂CH═CHCl 176 A1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O3-Iodo-propargyl 177 A1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O c-Pr 178 A1 4-CH₃H H 1 CH₃ H 2-CH₃ 1 O O c-Hex 179 A1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O2-CH₃-c-Pr 180 A2 — H H 1 CH₃ H — 1 O O CH₃ 181 A2 — H H 1 CH₃ H 2-Cl 1O O CH₃ 182 A2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 183 A2 2-Et H H 1 CH₃ H2-Cl 1 O O CH₃ 184 A2 2-CF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 185 A2 2-F H H 1CH₃ H 2-Cl 1 O O CH₃ 186 A2 2-Cl H H 1 CH₃ H 2-Cl 1 O O CH₃ 187 A22-OCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 188 A2 2-OEt H H 1 CH₃ H 2-Cl 1 O OCH₃ 189 A2 2-OCF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 190 A2 5-CH₃ H H 1 CH₃ H2-Cl 1 O O CH₃ 191 A2 5-Et H H 1 CH₃ H 2-Cl 1 O O CH₃ 192 A2 5-CF₃ H H 1CH₃ H 2-Cl 1 O O CH₃ 193 A2 5-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 194 A2 5-Cl HH 1 CH₃ H 2-Cl 1 O O CH₃ 195 A2 5-OCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 196 A25-OEt H H 1 CH₃ H 2-Cl 1 O O CH₃ 197 A2 5-OCF₃ H H 1 CH₃ H 2-Cl 1 O OCH₃ 198 A2 2,5-diCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 199 A2 2-Et-5-CH₃ H H 1CH₃ H 2-Cl 1 O O CH₃ 200 A2 2-CF₃-5-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 201 A22,5-diF H H 1 CH₃ H 2-Cl 1 O O CH₃ 202 A2 2-Cl-5-F H H 1 CH₃ H 2-Cl 1 OO CH₃ 203 A2 2,5-diOCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 204 A2 2-OEt-5-CH₃ HH 1 CH₃ H 2-Cl 1 O O CH₃ 205 A2 2-OCF₃-5-F H H 1 CH₃ H 2-Cl 1 O O CH₃206 A2 2-CH₃ H CH₃ 1 CH₃ H 2-Cl 1 O O CH₃ 207 A2 2-Et H CH₃ 1 CH₃ H 2-Cl1 O O CH₃ 208 A2 2-CH₃ H Et 1 CH₃ H 2-Cl 1 O O CH₃ 209 A2 2-CH₃ H i-Pr 1CH₃ H 2-Cl 1 O O CH₃ 210 A2 2-CH₃ CH₃ Et 1 CH₃ H 2-Cl 1 O O CH₃ 211 A22-CH₃ H F 1 CH₃ H 2-Cl 1 O O CH₃ 212 A2 2-CH₃ F F 1 CH₃ H 2-Cl 1 O O CH₃213 A2 2-CH₃ H CF₃ 1 CH₃ H 2-Cl 1 O O CH₃ 214 A2 2-CH₃ H c-Pr 1 CH₃ H2-Cl 1 O O CH₃ 215 A2 2-CH₃ —CH2CH2— 1 CH₃ H 2-Cl 1 O O CH₃ 216 A2 2-CH₃—CH2CH2CH2— 1 CH₃ H 2-Cl 1 O O CH₃ 217 A2 2-CH₃ —CH2CH(CH3)— 1 CH₃ H2-Cl 1 O O CH₃ 218 A2 2-CH₃ —CH2C(CH3)2— 1 CH₃ H 2-Cl 1 O O CH₃ 219 A22-CH₃ H H 1 H H 2-Cl 1 O O CH₃ 220 A2 2-CH₃ H H 1 Et H 2-Cl 1 O O CH₃221 A2 2-CH₃ H H 1 c-Pr H 2-Cl 1 O O CH₃ 222 A2 2-CH₃ H H 1 CH═CH₂ H2-Cl 1 O O CH₃ 223 A2 2-CH₃ H H 1 CH₂CH═CH₂ H 2-Cl 1 O O CH₃ 224 A22-CH₃ H H 1 ethynyl H 2-Cl 1 O O CH₃ 225 A2 2-CH₃ H H 1 Propargyl H 2-Cl1 O O CH₃ 226 A2 2-CH₃ H H 1 CF₃ H 2-Cl 1 O O CH₃ 227 A2 2-CH₃ H H 1CH═CHCl H 2-Cl 1 O O CH₃ 228 A2 2-CH₃ H H 1 3,3,2-tri-Iodo-allyl H 2-Cl1 O O CH₃ 229 A2 2-CH₃ H H 1 3-Iodopropargyl H 2-Cl 1 O O CH₃ 230 A22-CH₃ H H 1 CN H 2-Cl 1 O O CH₃ 231 A2 2-CF₃ H H 1 CN H 2-Cl 1 O O CH₃232 A2 2-CH₃ H H 1 NO₂ H 2-Cl 1 O O CH₃ 233 A2 2-CH₃ H H 1 NH₂ H 2-Cl 1O O CH₃ 234 A2 2-CH₃ H H 1 NHCH₃ H 2-Cl 1 O O CH₃ 235 A2 2-CH₃ H H 1N(CH₃)₂ H 2-Cl 1 O O CH₃

TABLE 5 236 A2 2-CH₃ H H 1 CH₃ CH₃ 2-Cl 1 O O CH₃ 237 A2 2-CH₃ H H 1 CH₃Et 2-Cl 1 O O CH₃ 238 A2 2-CH₃ H H 1 CH₃ CH₃CO 2-Cl 1 O O CH₃ 239 A22-CH₃ H H 1 CH₃ CH₃CH₂CO 2-Cl 1 O O CH₃ 240 A2 2-CH₃ H H 1 CH₃ PhCO 2-Cl1 O O CH₃ 241 A2 2-CH₃ H H 1 CH₃ 4-Cl—PhCO 2-Cl 1 O O CH₃ 242 A2 2-CH₃ HH 1 CH₃ PhCH₂CO 2-Cl 1 O O CH₃ 243 A2 2-CH₃ H H 1 CH₃ CHO 2-Cl 1 O O CH₃244 A2 2-CH₃ H H 1 CH₃ CH₃OCH₂ 2-Cl 1 O O CH₃ 245 A2 2-CH₃ H H 1 CH₃CH₃CH(OCH₃) 2-Cl 1 O O CH₃ 246 A2 2-CH₃ H H 1 CH₃ CH₃SO₂ 2-Cl 1 O O CH₃247 A2 2-CH₃ H H 1 CH₃ PhSO₂ 2-Cl 1 O O CH₃ 248 A2 2-CH₃ H H 1 CH₃4-CH₃—PhSO₂ 2-Cl 1 O O CH₃ 249 A2 2-CH₃ H H 1 CH₃ H 2-Cl 1 S O CH₃ 250A2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O S CH₃ 251 A2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O —CH₃ 252 A2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O NH CH₃ 253 A2 2-CH₃ H H 1 CH₃ H2-Cl 1 O NCH₃ CH₃ 254 A2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O H 255 A2 2-CH₃ H H1 CH₃ H 2-Cl 1 O O Et 256 A2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O n-Pr 257 A22-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₂CH═CH₂ 258 A2 2-CH₃ H H 1 CH₃ H 2-Cl 1 OO CH═CH₂ 259 A2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O Propargyl 260 A2 2-CH₃ H H1 CH₃ H 2-Cl 1 O O ethynyl 261 A2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O CF₃ 262A2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₂CF₃ 263 A2 2-CH₃ H H 1 CH₃ H 2-Cl 1 OO CF₂CF₃ 264 A2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O CF₂CF₂H 265 A2 2-CH₃ H H 1CH₃ H 2-Cl 1 O O CH₂CH═CHCl 266 A2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O3-Iodo-propargyl 267 A2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O c-Pr 268 A2 2-CH₃ HH 1 CH₃ H 2-Cl 1 O O c-Hex 269 A2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O2-CH₃-c-Pr 270 A2 — H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 271 A2 2-CH₃ H H 1 CH₃ H2-CH₃ 1 O O CH₃ 272 A2 2-Et H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 273 A2 2-CF₃ H H1 CH₃ H 2-CH₃ 1 O O CH₃ 274 A2 2-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 275 A22-Cl H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 278 A2 2-OCH₃ H H 1 CH₃ H 2-CH₃ 1 O OCH₃ 277 A2 2-OEt H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 278 A2 2-OCF₃ H H 1 CH₃ H2-CH₃ 1 O O CH₃ 279 A2 5-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 280 A2 5-Et H H1 CH₃ H 2-CH₃ 1 O O CH₃ 281 A2 5-CF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 282 A25-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 283 A2 5-Cl H H 1 CH₃ H 2-CH₃ 1 O O CH₃284 A2 5-OCH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 285 A2 5-OEt H H 1 CH₃ H 2-CH₃1 O O CH₃ 286 A2 5-OCF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 287 A2 2.5-diCH₃ H H1 CH₃ H 2-CH₃ 1 O O CH₃ 288 A2 2-Et-5-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃289 A2 2-CF₃5-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 290 A2 2,5-diF H H 1 CH₃ H2-CH₃ 1 O O CH₃ 291 A2 2-Cl-5-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 292 A22,5-diOCH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 293 A2 2-OEt-5-CH₃ H H 1 CH₃ H2-CH₃ 1 O O CH₃ 294 A2 2-OCF₃-5-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 295 A22-CH₃ H CH₃ 1 CH₃ H 2-CH₃ 1 O O CH₃ 296 A2 2-Et H CH₃ 1 CH₃ H 2-CH₃ 1 OO CH₃ 297 A2 2-CH₃ H Et 1 CH₃ H 2-CH₃ 1 O O CH₃

TABLE 6 298 A2 2-CH₃ H i-Pr 1 CH₃ H 2-CH₃ 1 O O CH₃ 299 A2 2-CH₃ CH₃ Et1 CH₃ H 2-CH₃ 1 O O CH₃ 300 A2 2-CH₃ H F 1 CH₃ H 2-CH₃ 1 O O CH₃ 301 A22-CH₃ F F 1 CH₃ H 2-CH₃ 1 O O CH₃ 302 A2 2-CH₃ H CF₃ 1 CH₃ H 2-CH₃ 1 O OCH₃ 303 A2 2-CH₃ H c-Pr 1 CH₃ H 2-CH₃ 1 O O CH₃ 304 A2 2-CH₃ —CH2CH2— 1CH₃ H 2-CH₃ 1 O O CH₃ 305 A2 2-CH₃ —CH2CH2CH2— 1 CH₃ H 2-CH₃ 1 O O CH₃306 A2 2-CH₃ —CH2CH(CH3)— 1 CH₃ H 2-CH₃ 1 O O CH₃ 307 A2 2-CH₃—CH2C(CH3)2— 1 CH₃ H 2-CH₃ 1 O O CH₃ 308 A2 2-CH₃ H H 1 H H 2-CH₃ 1 O OCH₃ 309 A2 2-CH₃ H H 1 Et H 2-CH₃ 1 O O CH₃ 310 A2 2-CH₃ H H 1 c-Pr H2-CH₃ 1 O O CH₃ 311 A2 2-CH₃ H H 1 CH═CH₂ H 2-CH₃ 1 O O CH₃ 312 A2 2-CH₃H H 1 CH₂CH═CH₂ H 2-CH₃ 1 O O CH₃ 313 A2 2-CH₃ H H 1 ethynyl H 2-CH₃ 1 OO CH₃ 314 A2 2-CH₃ H H 1 Propargyl H 2-CH₃ 1 O O CH₃ 315 A2 2-CH₃ H H 1CF₃ H 2-CH₃ 1 O O CH₃ 316 A2 2-CH₃ H H 1 CH═CHCl H 2-CH₃ 1 O O CH₃ 317A2 2-CH₃ H H 1 3,3,2-tri-Iodo-allyl H 2-CH₃ 1 O O CH₃ 318 A2 2-CH₃ H H 13-Iodopropargyl H 2-CH₃ 1 O O CH₃ 319 A2 2-CH₃ H H 1 CN H 2-CH₃ 1 O OCH₃ 320 A2 2-CF₃ H H 1 CN H 2-CH₃ 1 O O CH₃ 321 A2 2-CH₃ H H 1 NO₂ H2-CH₃ 1 O O CH₃ 322 A2 2-CH₃ H H 1 NH₂ H 2-CH₃ 1 O O CH₃ 323 A2 2-CH₃ HH 1 NHCH₃ H 2-CH₃ 1 O O CH₃ 324 A2 2-CH₃ H H 1 N(CH₃)₂ H 2-CH₃ 1 O O CH₃325 A2 2-CH₃ H H 1 CH₃ CH₃ 2-CH₃ 1 O O CH₃ 326 A2 2-CH₃ H H 1 CH₃ Et2-CH₃ 1 O O CH₃ 327 A2 2-CH₃ H H 1 CH₃ CH₃CO 2-CH₃ 1 O O CH₃ 328 A22-CH₃ H H 1 CH₃ CH₃CH₂CO 2-CH₃ 1 O O CH₃ 329 A2 2-CH₃ H H 1 CH₃ PhCO2-CH₃ 1 O O CH₃ 330 A2 2-CH₃ H H 1 CH₃ 4-Cl-PhCO 2-CH₃ 1 O O CH₃ 331 A22-CH₃ H H 1 CH₃ PhCH₂CO 2-CH₃ 1 O O CH₃ 332 A2 2-CH₃ H H 1 CH₃ CHO 2-CH₃1 O O CH₃ 333 A2 2-CH₃ H H 1 CH₃ CH₃OCH₂ 2-CH₃ 1 O O CH₃ 334 A2 2-CH₃ HH 1 CH₃ CH₃CH(OCH₃) 2-CH₃ 1 O O CH₃ 335 A2 2-CH₃ H H 1 CH₃ CH₃SO₂ 2-CH₃1 O O CH₃ 336 A2 2-CH₃ H H 1 CH₃ PhSO₂ 2-CH₃ 1 O O CH₃ 337 A2 2-CH₃ H H1 CH₃ 4-CH₃—PhSO₂ 2-CH₃ 1 O O CH₃ 338 A2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 S OCH₃ 339 A2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O S CH₃ 340 A2 2-CH₃ H H 1 CH₃ H2-CH₃ 1 O — CH₃ 341 A2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O NH CH₃ 342 A2 2-CH₃ HH 1 CH₃ H 2-CH₃ 1 O NCH₃ CH₃ 343 A2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O H 344A2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O Et 345 A2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O On-Pr 346 A2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CH═CH₂ 347 A2 2-CH₃ H H 1CH₃ H 2-CH₃ 1 O O CH═CH₂ 348 A2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O Propargyl349 A2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O ethynyl 350 A2 2-CH₃ H H 1 CH₃ H2-CH₃ 1 O O CF₃ 351 A2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CF₃ 352 A2 2-CH₃H H 1 CH₃ H 2-CH₃ 1 O O CF₂CF₃ 353 A2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O OCF₂CF₂H 354 A2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CH═CHCl 355 A2 2-CH₃ H H1 CH₃ H 2-CH₃ 1 O O 3-Iodo-propargyl 356 A2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 OO c-Pr 357 A2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O c-Hex 358 A2 2-CH₃ H H 1 CH₃H 2-CH₃ 1 O O 2-CH₃-c-Pr 359 B1 — H H 1 CH₃ H — 0 O O CH₃

TABLE 7 360 B1 — H H 1 CH₃ H 2-Cl 1 O O CH₃ 361 B1 4-CH₃ H H 1 CH₃ H2-Cl 1 O O CH₃ 362 B1 4-Et H H 1 CH₃ H 2-Cl 1 O O CH₃ 363 B1 4-CF₃ H H 1CH₃ H 2-Cl 1 O O CH₃ 364 B1 4-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 365 B1 4-Cl HH 1 CH₃ H 2-Cl 1 O O CH₃ 366 B1 4-OCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 367 B14-OEt H H 1 CH₃ H 2-Cl 1 O O CH₃ 368 B1 4-OCF₃ H H 1 CH₃ H 2-Cl 1 O OCH₃ 369 B1 5-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 370 B1 5-Et H H 1 CH₃ H 2-Cl1 O O CH₃ 371 B1 5-CF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 372 B1 5-F H H 1 CH₃ H2-Cl 1 O O CH₃ 373 B1 5-Cl H H 1 CH₃ H 2-Cl 1 O O CH₃ 374 B1 5-OCH₃ H H1 CH₃ H 2-Cl 1 O O CH₃ 375 B1 5-OEt H H 1 CH₃ H 2-Cl 1 O O CH₃ 376 B15-OCF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 377 B1 4,5-diCH₃ H H 1 CH₃ H 2-Cl 1 OO CH₃ 378 B1 4-Et-5-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 379 B1 4-CF₃-5-F H H1 CH₃ H 2-Cl 1 O O CH₃ 380 B1 4,5-diF H H 1 CH₃ H 2-Cl 1 O O CH₃ 381 B14-Cl-5-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 382 B1 4,5-diOCH₃ H H 1 CH₃ H 2-Cl 1O O CH₃ 383 B1 4-OEt-5-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 384 B1 4-OCF₃-5-FH H 1 CH₃ H 2-Cl 1 O O CH₃ 385 B1 4-CH₃ H CH₃ 1 CH₃ H 2-Cl 1 O O CH₃ 386B1 4-Et H CH₃ 1 CH₃ H 2-Cl 1 O O CH₃ 387 B1 4-CH₃ H Et 1 CH₃ H 2-Cl 1 OO CH₃ 388 B1 4-CH₃ H i-Pr 1 CH₃ H 2-Cl 1 O O CH₃ 389 B1 4-CH₃ CH₃ Et 1CH₃ H 2-Cl 1 O O CH₃ 390 B1 4-CH₃ H F 1 CH₃ H 2-Cl 1 O O CH₃ 391 B14-CH₃ F F 1 CH₃ H 2-Cl 1 O O CH₃ 392 B1 4-CH₃ H CF₃ 1 CH₃ H 2-Cl 1 O OCH₃ 393 B1 4-CH₃ H c-Pr 1 CH₃ H 2-Cl 1 O O CH₃ 394 B1 4-CH₃ —CH2CH2— 1CH₃ H 2-Cl 1 O O CH₃ 395 B1 4-CH₃ —CH2CH2CH2— 1 CH₃ H 2-Cl 1 O O CH₃ 396B1 4-CH₃ —CH2CH(CH3)— 1 CH₃ H 2-Cl 1 O O CH₃ 397 B1 4-CH₃ —CH2C(CH3)2— 1CH₃ H 2-Cl 1 O O CH₃ 398 B1 4-CH₃ H H 1 H H 2-Cl 1 O O CH₃ 399 B1 4-CH₃H H 1 Et H 2-Cl 1 O O CH₃ 400 B1 4-CH₃ H H 1 c-Pr H 2-Cl 1 O O CH₃ 401B1 4-CH₃ H H 1 CH═CH₂ H 2-Cl 1 O O CH₃ 402 B1 4-CH₃ H H 1 CH₂CH═CH₂ H2-Cl 1 O O CH₃ 403 B1 4-CH₃ H H 1 ethynyl H 2-Cl 1 O O CH₃ 404 B1 4-CH₃H H 1 Propargyl H 2-Cl 1 O O CH₃ 405 B1 4-CH₃ H H 1 CF₃ H 2-Cl 1 O O CH₃406 B1 4-CH₃ H H 1 CH═CHCl H 2-Cl 1 O O CH₃ 407 B1 4-CH₃ H H 13,3,2-tri-Iodo-allyl H 2-Cl 1 O O CH₃ 408 B1 4-CH₃ H H 1 3-IodopropargylH 2-Cl 1 O O CH₃ 409 B1 4-CH₃ H H 1 CN H 2-Cl 1 O O CH₃ 410 B1 4-CF3 H H1 CN H 2-Cl 1 O O CH₃ 411 B1 4-CH₃ H H 1 NO₂ H 2-Cl 1 O O CH₃ 412 B14-CH₃ H H 1 NH₂ H 2-Cl 1 O O CH₃ 413 B1 4-CH₃ H H 1 NHCH₃ H 2-Cl 1 O OCH₃ 414 B1 4-CH₃ H H 1 N(CH₃)₂ H 2-Cl 1 O O CH₃ 415 B1 4-CH₃ H H 1 CH₃CH₃ 2-Cl 1 O O CH₃ 416 B1 4-CH₃ H H 1 CH₃ Et 2-Cl 1 O O CH₃ 417 B1 4-CH₃H H 1 CH₃ CH₃CO 2-Cl 1 O O CH₃ 418 B1 4-CH₃ H H 1 CH₃ CH₃CH₂CO 2-Cl 1 OO CH₃ 419 B1 4-CH₃ H H 1 CH₃ PhCO 2-Cl 1 O O CH₃

TABLE 8 420 B1 4-CH₃ H H 1 CH₃ 4-Cl-PhCO 2-Cl 1 O O CH₃ 421 B1 4-CH₃ H H1 CH₃ PhCH₂CO 2-Cl 1 O O CH₃ 422 B1 4-CH₃ H H 1 CH₃ CHO 2-Cl 1 O O CH₃423 B1 4-CH₃ H H 1 CH₃ CH₃OCH₂ 2-Cl 1 O O CH₃ 424 B1 4-CH₃ H H 1 CH₃CH₃CH(OCH₃) 2-Cl 1 O O CH₃ 425 B1 4-CH₃ H H 1 CH₃ CH₃SO₂ 2-Cl 1 O O CH₃426 B1 4-CH₃ H H 1 CH₃ PhSO₂ 2-Cl 1 O O CH₃ 427 B1 4-CH₃ H H 1 CH₃4-CH₃-PhSO₂ 2-Cl 1 O O CH₃ 428 B1 4-CH₃ H H 1 CH₃ H 2-Cl 1 S O CH₃ 429B1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O S CH₃ 430 B1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O —CH₃ 431 B1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O NH CH₃ 432 B1 4-CH₃ H H 1 CH₃ H2-Cl 1 O NCH₃ CH₃ 433 B1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O H 434 B1 4-CH₃ H H1 CH₃ H 2-Cl 1 O O Et 435 B1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O n-Pr 436 B14-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₂CH═CH₂ 437 B1 4-CH₃ H H 1 CH₃ H 2-Cl 1 OO CH═CH₂ 438 B1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O Propargyl 439 B1 4-CH₃ H H1 CH₃ H 2-Cl 1 O O ethynyl 440 B1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O CF₃ 441B1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₂CF₃ 442 B1 4-CH₃ H H 1 CH₃ H 2-Cl 1 OO CF₂CF₃ 443 B1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O CF₂CF₂H 444 B1 4-CH₃ H H 1CH₃ H 2-Cl 1 O O CH₂CH═CHCl 445 B1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O3-Iodo-propargyl 446 B1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O c-Pr 447 B1 4-CH₃ HH 1 CH₃ H 2-Cl 1 O O c-Hex 448 B1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O2-CH₃-c-Pr 449 B1 — H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 450 B1 4-CH₃ H H 1 CH₃ H2-CH₃ 1 O O CH₃ 451 B1 4-Et H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 452 B1 4-CF₃ H H1 CH₃ H 2-CH₃ 1 O O CH₃ 453 B1 4-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 454 B14-Cl H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 455 B1 4-OCH₃ H H 1 CH₃ H 2-CH₃ 1 O OCH₃ 456 B1 4-OEt H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 457 B1 4-OCF₃ H H 1 CH₃ H2-CH₃ 1 O O CH₃ 458 B1 5-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 459 B1 5-Et H H1 CH₃ H 2-CH₃ 1 O O CH₃ 460 B1 5-CF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 461 B15-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 462 B1 5-Cl H H 1 CH₃ H 2-CH₃ 1 O O CH₃463 B1 5-OCH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 464 B1 5-OEt H H 1 CH₃ H 2-CH₃1 O O CH₃ 465 B1 5-OCF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 466 B1 4,5-diCH₃ H H1 CH₃ H 2-CH₃ 1 O O CH₃ 467 B1 4-Et-5-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃468 B1 4-CF₃-5-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 469 B1 4,5-diF H H 1 CH₃ H2-CH₃ 1 O O CH₃ 470 B1 4-Cl-5-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 471 B14,5-diOCH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 472 B1 4-OEt-5-CH₃ H H 1 CH₃ H2-CH₃ 1 O O CH₃ 473 B1 4-OCF₃-5-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 474 B14-CH₃ H CH₃ 1 CH₃ H 2-CH₃ 1 O O CH₃ 475 B1 4-Et H CH₃ 1 CH₃ H 2-CH₃ 1 OO CH₃ 476 B1 4-CH₃ H Et 1 CH₃ H 2-CH₃ 1 O O CH₃ 477 B1 4-CH₃ H i-Pr 1CH₃ H 2-CH₃ 1 O O CH₃ 478 B1 4-CH₃ CH₃ Et 1 CH₃ H 2-CH₃ 1 O O CH₃ 479 B14-CH₃ H F 1 CH₃ H 2-CH₃ 1 O O CH₃

TABLE 9 480 B1 4-CH₃ F F 1 CH₃ H 2-CH₃ 1 O O CH₃ 481 B1 4-CH₃ H CF₃ 1CH₃ H 2-CH₃ 1 O O CH₃ 482 B1 4-CH₃ H c-Pr 1 CH₃ H 2-CH₃ 1 O O CH₃ 483 B14-CH₃ —CH2CH2— 1 CH₃ H 2-CH₃ 1 O O CH₃ 484 B1 4-CH₃ —CH2CH2CH2— 1 CH₃ H2-CH₃ 1 O O CH₃ 485 B1 4-CH₃ —CH2CH(CH3)— 1 CH₃ H 2-CH₃ 1 O O CH₃ 486 B14-CH₃ —CH2C(CH3)2— 1 CH₃ H 2-CH₃ 1 O O CH₃ 487 B1 4-CH₃ H H 1 H H 2-CH₃1 O O CH₃ 488 B1 4-CH₃ H H 1 Et H 2-CH₃ 1 O O CH₃ 489 B1 4-CH₃ H H 1c-Pr H 2-CH₃ 1 O O CH₃ 490 B1 4-CH₃ H H 1 CH═CH₂ H 2-CH₃ 1 O O CH₃ 491B1 4-CH₃ H H 1 CH₂CH═CH₂ H 2-CH₃ 1 O O CH₃ 492 B1 4-CH₃ H H 1 ethynyl H2-CH₃ 1 O O CH₃ 493 B1 4-CH₃ H H 1 Propargyl H 2-CH₃ 1 O O CH₃ 494 B14-CH₃ H H 1 CF₃ H 2-CH₃ 1 O O CH₃ 495 B1 4-CH₃ H H 1 CH═CHCl H 2-CH₃ 1 OO CH₃ 496 B1 4-CH₃ H H 1 3,3,2-tri-Iodo-allyl H 2-CH₃ 1 O O CH₃ 497 B14-CH₃ H H 1 3-Iodopropargyl H 2-CH₃ 1 O O CH₃ 498 B1 4-CH₃ H H 1 CN H2-CH₃ 1 O O CH₃ 499 B1 4-CF₃ H H 1 CN H 2-CH₃ 1 O O CH₃ 500 B1 4-CH₃ H H1 NO₂ H 2-CH₃ 1 O O CH₃ 501 B1 4-CH₃ H H 1 NH₂ H 2-CH₃ 1 O O CH₃ 502 B14-CH₃ H H 1 NHCH₃ H 2-CH₃ 1 O O CH₃ 503 B1 4-CH₃ H H 1 N(CH₃)₂ H 2-CH₃ 1O O CH₃ 504 B1 4-CH₃ H H 1 CH₃ CH₃ 2-CH₃ 1 O O CH₃ 505 B1 4-CH₃ H H 1CH₃ Et 2-CH₃ 1 O O CH₃ 506 B1 4-CH₃ H H 1 CH₃ CH₃CO 2-CH₃ 1 O O CH₃ 507B1 4-CH₃ H H 1 CH₃ CH₃CH₂CO 2-CH₃ 1 O O CH₃ 508 B1 4-CH₃ H H 1 CH₃ PhCO2-CH₃ 1 O O CH₃ 509 B1 4-CH₃ H H 1 CH₃ 4-Cl-PhCO 2-CH₃ 1 O O CH₃ 510 B14-CH₃ H H 1 CH₃ PhCH₂CO 2-CH₃ 1 O O CH₃ 511 B1 4-CH₃ H H 1 CH₃ CHO 2-CH₃1 O O CH₃ 512 B1 4-CH₃ H H 1 CH₃ CH₃OCH₂ 2-CH₃ 1 O O CH₃ 513 B1 4-CH₃ HH 1 CH₃ CH₃CH(OCH₃) 2-CH₃ 1 O O CH₃ 514 B1 4-CH₃ H H 1 CH₃ CH₃SO₂ 2-CH₃1 O O CH₃ 515 B1 4-CH₃ H H 1 CH₃ PhSO₂ 2-CH₃ 1 O O CH₃ 516 B1 4-CH₃ H H1 CH₃ 4-CH₃-PhSO₂ 2-CH₃ 1 O O CH₃ 517 B1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 S OCH₃ 518 B1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O S CH₃ 519 B1 4-CH₃ H H 1 CH₃ H2-CH₃ 1 O — CH₃ 520 B1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O NH CH₃ 521 B1 4-CH₃ HH 1 CH₃ H 2-CH₃ 1 O NCH₃ CH₃ 522 B1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O H 523B1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O Et 524 B1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O On-Pr 525 B1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CH═CH₂ 526 B1 4-CH₃ H H 1CH₃ H 2-CH₃ 1 O O CH═CH₂ 527 B1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O Propargyl528 B1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O ethynyl 529 B1 4-CH₃ H H 1 CH₃ H2-CH₃ 1 O O CF₃ 530 B1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CF₃ 531 B1 4-CH₃H H 1 CH₃ H 2-CH₃ 1 O O CF₂CF₃ 532 B1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O OCF₂CF₂H 533 B1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CH═CHCl 534 B1 4-CH₃ H H1 CH₃ H 2-CH₃ 1 O O 3-Iodo-propargyl 535 B1 4-CH₃ H H 1 CH₃ H 3-CH₃ 1 OO c-Pr 536 B1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O c-Hex 537 B1 4-CH₃ H H 1 CH₃H 2-CH₃ 1 O O 2-CH₃-c-Pr 538 B2 — H H 1 CH₃ H — 0 O O CH₃ 539 B2 — H H 1CH₃ H 2-Cl 1 O O CH₃ 540 B2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 541 B2 2-EtH H 1 CH₃ H 2-Cl 1 O O CH₃

TABLE 10 542 B2 2-CF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 543 B2 2-F H H 1 CH₃ H2-Cl 1 O O CH₃ 544 B2 2-Cl H H 1 CH₃ H 2-Cl 1 O O CH₃ 545 B2 2-OCH₃ H H1 CH₃ H 2-Cl 1 O O CH₃ 546 B2 2-OEt H H 1 CH₃ H 2-Cl 1 O O CH₃ 547 B22-OCF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 548 B2 5-CH₃ H H 1 CH₃ H 2-Cl 1 O OCH₃ 549 B2 5-Et H H 1 CH₃ H 2-Cl 1 O O CH₃ 550 B2 5-CF₃ H H 1 CH₃ H 2-Cl1 O O CH₃ 551 B2 5-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 552 B2 5-Cl H H 1 CH₃ H2-Cl 1 O O CH₃ 553 B2 5-OCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 554 B2 5-OEt H H1 CH₃ H 2-Cl 1 O O CH₃ 555 B2 5-OCF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 556 B22,5-diCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 557 B2 2-Et-5-CH₃ H H 1 CH₃ H 2-Cl1 O O CH₃ 558 B2 2-CF₃-5-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 559 B2 2,5-diF H H1 CH₃ H 2-Cl 1 O O CH₃ 560 B2 2-Cl-5-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 561 B22,5-diOCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 562 B2 2-OEt-5-CH₃ H H 1 CH₃ H2-Cl 1 O O CH₃ 563 B2 2-OCF₃-5-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 564 B2 2-CH₃H CH₃ 1 CH₃ H 2-Cl 1 O O CH₃ 565 B2 2-Et H CH₃ 1 CH₃ H 2-Cl 1 O O CH₃566 B2 2-CH₃ H Et 1 CH₃ H 2-Cl 1 O O CH₃ 567 B2 2-CH₃ H i-Pr 1 CH₃ H2-Cl 1 O O CH₃ 568 B2 2-CH₃ CH₃ Et 1 CH₃ H 2-Cl 1 O O CH₃ 569 B2 2-CH₃ HF 1 CH₃ H 2-Cl 1 O O CH₃ 570 B2 2-CH₃ F F 1 CH₃ H 2-Cl 1 O O CH₃ 571 B22-CH₃ H CF₃ 1 CH₃ H 2-Cl 1 O O CH₃ 572 B2 2-CH₃ H c-Pr 1 CH₃ H 2-Cl 1 OO CH₃ 573 B2 2-CH₃ —CH2CH2— 1 CH₃ H 2-Cl 1 O O CH₃ 574 B2 2-CH₃—CH2CH2CH2— 1 CH₃ H 2-Cl 1 O O CH₃ 575 B2 2-CH₃ —CH2CH(CH3)— 1 CH₃ H2-Cl 1 O O CH₃ 576 B2 2-CH₃ —CH2C(CH3)2— 1 CH₃ H 2-Cl 1 O O CH₃ 577 B22-CH₃ H H 1 H H 2-Cl 1 O O CH₃ 578 B2 2-CH₃ H H 1 Et H 2-Cl 1 O O CH₃579 B2 2-CH₃ H H 1 c-Pr H 2-Cl 1 O O CH₃ 580 B2 2-CH₃ H H 1 CH═CH₂ H2-Cl 1 O O CH₃ 581 B2 2-CH₃ H H 1 CH₂CH═CH₂ H 2-Cl 1 O O CH₃ 582 B22-CH₃ H H 1 ethynyl H 2-Cl 1 O O CH₃ 583 B2 2-CH₃ H H 1 Propargyl H 2-Cl1 O O CH₃ 584 B2 2-CH₃ H H 1 CF₃ H 2-Cl 1 O O CH₃ 585 B2 2-CH₃ H H 1CH═CHCl H 2-Cl 1 O O CH₃ 586 B2 2-CH₃ H H 1 3,3,2-tri-Iodo-allyl H 2-Cl1 O O CH₃ 587 B2 2-CH₃ H H 1 3-Iodopropargyl H 2-Cl 1 O O CH₃ 588 B22-CH₃ H H 1 CN H 2-Cl 1 O O CH₃ 589 B2 2-CF₃ H H 1 CN H 2-Cl 1 O O CH₃590 B2 2-CH₃ H H 1 NO₂ H 2-Cl 1 O O CH₃ 591 B2 2-CH₃ H H 1 NH₂ H 2-Cl 1O O CH₃ 592 B2 2-CH₃ H H 1 NHCH₃ H 2-Cl 1 O O CH₃ 593 B2 2-CH₃ H H 1N(CH₃)₂ H 2-Cl 1 O O CH₃ 594 B2 2-CH₃ H H 1 CH₃ CH₃ 2-Cl 1 O O CH₃ 595B2 2-CH₃ H H 1 CH₃ Et 2-Cl 1 O O CH₃ 596 B2 2-CH₃ H H 1 CH₃ CH₃CO 2-Cl 1O O CH₃ 597 B2 2-CH₃ H H 1 CH₃ CH₃CH₂CO 2-Cl 1 O O CH₃ 598 B2 2-CH₃ H H1 CH₃ PhCO 2-Cl 1 O O CH₃ 599 B2 2-CH₃ H H 1 CH₃ 4-Cl-PhCO 2-Cl 1 O OCH₃ 600 B2 2-CH₃ H H 1 CH₃ PhCH₂CO 2-Cl 1 O O CH₃ 601 B2 2-CH₃ H H 1 CH₃CHO 2-Cl 1 O O CH₃ 602 B2 2-CH₃ H H 1 CH₃ CH₃OCH₂ 2-Cl 1 O O CH₃ 603 B22-CH₃ H H 1 CH₃ CH₃CH(OCH₃) 2-Cl 1 O O CH₃

TABLE 11 604 B2 2-CH₃ H H 1 CH₃ CH₃SO₂ 2-Cl 1 O O CH₃ 605 B2 2-CH₃ H H 1CH₃ PhSO₂ 2-Cl 1 O O CH₃ 606 B2 2-CH₃ H H 1 CH₃ 4-CH₃-PhSO₂ 2-Cl 1 O OCH₃ 607 B2 2-CH₃ H H 1 CH₃ H 2-Cl 1 S O CH₃ 608 B2 2-CH₃ H H 1 CH₃ H2-Cl 1 O S CH₃ 609 B2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O — CH₃ 610 B2 2-CH₃ H H1 CH₃ H 2-Cl 1 O NH CH₃ 611 B2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O NCH₃ CH₃ 612B2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O H 613 B2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O Et614 B2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O n-Pr 615 B2 2-CH₃ H H 1 CH₃ H 2-Cl 1O O CH₂CH═CH₂ 616 B2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH═CH₂ 617 B2 2-CH₃ HH 1 CH₃ H 2-Cl 1 O O Propargyl 618 B2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O Oethynyl 619 B2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O CF₃ 620 B2 2-CH₃ H H 1 CH₃ H2-Cl 1 O O CH₂CF₃ 621 B2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O CF₃CF₃ 622 B22-CH₃ H H 1 CH₃ H 2-Cl 1 O O CF₂CF₂H 623 B2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O OCH₂CH═CHCl 624 B2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O 3-Iodo-propargyl 625 B22-CH₃ H H 1 CH₃ H 2-Cl 1 O O c-Pr 626 B2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O Oc-Hex 627 B2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O 2-CH₃-c-Pr 628 B2 — H H 1 CH₃H 2-CH₃ 1 O O CH₃ 629 B2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 630 B2 2-Et HH 1 CH₃ H 2-CH₃ 1 O O CH₃ 631 B2 2-CF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 632B2 2-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 633 B2 2-Cl H H 1 CH₃ H 2-CH₃ 1 O OCH₃ 634 B2 2-OCH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 635 B2 2-OEt H H 1 CH₃ H2-CH₃ 1 O O CH₃ 636 B2 2-OCF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 637 B2 5-CH₃ HH 1 CH₃ H 2-CH₃ 1 O O CH₃ 638 B2 5-Et H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 639 B25-CF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 640 B2 5-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃641 B2 5-Cl H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 642 B2 5-OCH₃ H H 1 CH₃ H 2-CH₃1 O O CH₃ 643 B2 5-OEt H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 644 B2 5-OCF₃ H H 1CH₃ H 2-CH₃ 1 O O CH₃ 645 B2 2,5-diCH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 646B2 2-Et-5-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 647 B2 2-CF₃-5-F H H 1 CH₃ H2-CH₃ 1 O O CH₃ 648 B2 2,5-diF H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 649 B22-Cl-5-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 650 B2 2,5-diOCH₃ H H 1 CH₃ H 2-CH₃1 O O CH₃ 651 B2 2-OEt-5-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 652 B22-OCF₃-5-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 653 B2 2-CH₃ H CH₃ 1 CH₃ H 2-CH₃1 O O CH₃ 654 B2 2-Et H CH₃ 1 CH₃ H 2-CH₃ 1 O O CH₃ 655 B2 2-CH₃ H Et 1CH₃ H 2-CH₃ 1 O O CH₃ 656 B2 2-CH₃ H i-Pr 1 CH₃ H 2-CH₃ 1 O O CH₃ 657 B22-CH₃ CH₃ Et 1 CH₃ H 2-CH₃ 1 O O CH₃ 658 B2 2-CH₃ H F 1 CH₃ H 2-CH₃ 1 OO CH₃ 659 B2 2-CH₃ F F 1 CH₃ H 2-CH₃ 1 O O CH₃ 660 B2 2-CH₃ H CF₃ 1 CH₃H 2-CH₃ 1 O O CH₃ 661 B2 2-CH₃ H c-Pr 1 CH₃ H 2-CH₃ 1 O O CH₃ 662 B22-CH₃ —CH2CH2— 1 CH₃ H 2-CH₃ 1 O O CH₃ 663 B2 2-CH₃ —CH2CH2CH2— 1 CH₃ H2-CH₃ 1 O O CH₃ 664 B2 2-CH₃ —CH2CH(CH3)— 1 CH₃ H 2-CH₃ 1 O O CH₃ 665 B22-CH₃ —CH2C(CH3)2— 1 CH₃ H 2-CH₃ 1 O O CH₃

TABLE 12 666 B2 2-CH₃ H H 1 H H 2-CH₃ 1 O O CH₃ 667 B2 2-CH₃ H H 1 Et H2-CH₃ 1 O O CH₃ 668 B2 2-CH₃ H H 1 c-Pr H 2-CH₃ 1 O O CH₃ 669 B2 2-CH₃ HH 1 CH═CH₂ H 2-CH₃ 1 O O CH₃ 670 B2 2-CH₃ H H 1 CH₂CH═CH₂ H 2-CH₃ 1 O OCH₃ 671 B2 2-CH₃ H H 1 ethynyl H 2-CH₃ 1 O O CH₃ 672 B2 2-CH₃ H H 1Propargyl H 2-CH₃ 1 O O CH₃ 673 B2 2-CH₃ H H 1 CF₃ H 2-CH₃ 1 O O CH₃ 674B2 2-CH₃ H H 1 CH═CHCl H 2-CH₃ 1 O O CH₃ 675 B2 2-CH₃ H H 13,3,2-tri-Iodo-allyl H 2-CH₃ 1 O O CH₃ 676 B2 2-CH₃ H H 13-Iodopropargyl H 2-CH₃ 1 O O CH₃ 677 B2 2-CH₃ H H 1 CN H 2-CH₃ 1 O OCH₃ 678 B2 2-CF₃ H H 1 CN H 2-CH₃ 1 O O CH₃ 679 B2 2-CH₃ H H 1 NO₂ H2-CH₃ 1 O O CH₃ 680 B2 2-CH₃ H H 1 NH₂ H 2-CH₃ 1 O O CH₃ 681 B2 2-CH₃ HH 1 NHCH₃ H 2-CH₃ 1 O O CH₃ 682 B2 2-CH₃ H H 1 N(CH₃)₂ H 2-CH₃ 1 O O CH₃683 B2 2-CH₃ H H 1 CH₃ CH₃ 2-CH₃ 1 O O CH₃ 684 B2 2-CH₃ H H 1 CH₃ Et2-CH₃ 1 O O CH₃ 685 B2 2-CH₃ H H 1 CH₃ CH₃CO 2-CH₃ 1 O O CH₃ 686 B22-CH₃ H H 1 CH₃ CH₃CH₂CO 2-CH₃ 1 O O CH₃ 687 B2 2-CH₃ H H 1 CH₃ PhCO2-CH₃ 1 O O CH₃ 688 B2 2-CH₃ H H 1 CH₃ 4-Cl-PhCO 2-CH₃ 1 O O CH₃ 689 B22-CH₃ H H 1 CH₃ PhCH₂CO 2-CH₃ 1 O O CH₃ 690 B2 2-CH₃ H H 1 CH₃ CHO 2-CH₃1 O O CH₃ 691 B2 2-CH₃ H H 1 CH₃ CH₃OCH₂ 2-CH₃ 1 O O CH₃ 692 B2 2-CH₃ HH 1 CH₃ CH₃CH(OCH₃) 2-CH₃ 1 O O CH₃ 693 B2 2-CH₃ H H 1 CH₃ CH₃SO₂ 2-CH₃1 O O CH₃ 694 B2 2-CH₃ H H 1 CH₃ PhSO₂ 2-CH₃ 1 O O CH₃ 695 B2 2-CH₃ H H1 CH₃ 4-CH₃-PhSO₂ 2-CH₃ 1 O O CH₃ 696 B2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 S OCH₃ 697 B2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O S CH₃ 698 B2 2-CH₃ H H 1 CH₃ H2-CH₃ 1 O — CH₃ 699 B2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O NH CH₃ 700 B2 2-CH₃ HH 1 CH₃ H 2-CH₃ 1 O NCH₃ CH₃ 701 B2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O H 702B2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O Et 703 B2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O On-Pr 704 B2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CH═CH₂ 705 B2 2-CH₃ H H 1CH₃ H 2-CH₃ 1 O O CH═CH₂ 706 B2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O Propargyl707 B2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O ethynyl 708 B2 2-CH₃ H H 1 CH₃ H2-CH₃ 1 O O CF₃ 709 B2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CF₃ 710 B2 2-CH₃H H 1 CH₃ H 2-CH₃ 1 O O CF₂CF₃ 711 B2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O OCF₂CF₂H 712 B2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CH═CHCl 713 B2 2-CH₃ H H1 CH₃ H 2-CH₃ 1 O O 3-Iodo-propargyl 714 B2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 OO c-Pr 715 B2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O c-Hex 716 B2 2-CH₃ H H 1 CH₃H 2-CH₃ 1 O O 2-CH₃-c-Pr 717 C1 — H H 1 CH₃ H — 0 O O CH₃ 718 C1 — H H 1CH₃ H 2-Cl 1 O O CH₃ 719 C1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 720 C1 4-EtH H 1 CH₃ H 2-Cl 1 O O CH₃ 721 C1 4-CF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 722C1 4-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 723 C1 4-Cl H H 1 CH₃ H 2-Cl 1 O O CH₃724 C1 4-OCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 725 C1 4-OEt H H 1 CH₃ H 2-Cl 1O O CH₃ 726 C1 4-OCF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 727 C1 5-CH₃ H H 1 CH₃H 2-Cl 1 O O CH₃

TABLE 13 728 C1 5-Et H H 1 CH₃ H 2-Cl 1 O O CH₃ 729 C1 5-CF₃ H H 1 CH₃ H2-Cl 1 O O CH₃ 730 C1 5-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 731 C1 5-Cl H H 1CH₃ H 2-Cl 1 O O CH₃ 732 C1 5-OCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 733 C15-OEt H H 1 CH₃ H 2-Cl 1 O O CH₃ 734 C1 5-OCF₃ H H 1 CH₃ H 2-Cl 1 O OCH₃ 735 C1 4,5-diCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 736 C1 4-Et-5-CH₃ H H 1CH₃ H 2-Cl 1 O O CH₃ 737 C1 4-CF₃-5-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 738 C14,5-diF H H 1 CH₃ H 2-Cl 1 O O CH₃ 739 C1 4-Cl-5-F H H 1 CH₃ H 2-Cl 1 OO CH₃ 740 C1 4,5-diOCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 741 C1 4-OEt-5-CH₃ HH 1 CH₃ H 2-Cl 1 O O CH₃ 742 C1 4-OCF₃-5-F H H 1 CH₃ H 2-Cl 1 O O CH₃743 C1 4-CH₃ H CH₃ 1 CH₃ H 2-Cl 1 O O CH₃ 744 C1 4-Et H CH₃ 1 CH₃ H 2-Cl1 O O CH₃ 745 C1 4-CH₃ H Et 1 CH₃ H 2-Cl 1 O O CH₃ 746 C1 4-CH₃ H i-Pr 1CH₃ H 2-Cl 1 O O CH₃ 747 C1 4-CH₃ CH₃ Et 1 CH₃ H 2-Cl 1 O O CH₃ 748 C14-CH₃ H F 1 CH₃ H 2-Cl 1 O O CH₃ 749 C1 4-CH₃ F F 1 CH₃ H 2-Cl 1 O O CH₃750 C1 4-CH₃ H CF₃ 1 CH₃ H 2-Cl 1 O O CH₃ 751 C1 4-CH₃ H c-Pr 1 CH₃ H2-Cl 1 O O CH₃ 752 C1 4-CH₃ —CH2CH2— 1 CH₃ H 2-Cl 1 O O CH₃ 753 C1 4-CH₃—CH2CH2CH2— 1 CH₃ H 2-Cl 1 O O CH₃ 754 C1 4-CH₃ —CH2CH(CH3)— 1 CH₃ H2-Cl 1 O O CH₃ 755 C1 4-CH₃ —CH2C(CH3)2— 1 CH₃ H 2-Cl 1 O O CH₃ 756 C14-CH₃ H H 1 H H 2-Cl 1 O O CH₃ 757 C1 4-CH₃ H H 1 Et H 2-Cl 1 O O CH₃758 C1 4-CH₃ H H 1 c-Pr H 2-Cl 1 O O CH₃ 759 C1 4-CH₃ H H 1 CH═CH₂ H2-Cl 1 O O CH₃ 760 C1 4-CH₃ H H 1 CH₂CH═CH₂ H 2-Cl 1 O O CH₃ 761 C14-CH₃ H H 1 ethynyl H 2-Cl 1 O O CH₃ 762 C1 4-CH₃ H H 1 Propargyl H 2-Cl1 O O CH₃ 763 C1 4-CH₃ H H 1 CF₃ H 2-Cl 1 O O CH₃ 764 C1 4-CH₃ H H 1CH═CHCl H 2-Cl 1 O O CH₃ 765 C1 4-CH₃ H H 1 3,3,2-tri-Iodo-allyl H 2-Cl1 O O CH₃ 766 C1 4-CH₃ H H 1 3-Iodopropargyl H 2-Cl 1 O O CH₃ 767 C14-CH₃ H H 1 CN H 2-Cl 1 O O CH₃ 768 C1 4-CF₃ H H 1 CN H 2-Cl 1 O O CH₃769 C1 4-CH₃ H H 1 NO₂ H 2-Cl 1 O O CH₃ 770 C1 4-CH₃ H H 1 NH₂ H 2-Cl 1O O CH₃ 771 C1 4-CH₃ H H 1 NHCH₃ H 2-Cl 1 O O CH₃ 772 C1 4-CH₃ H H 1N(CH₃)₂ H 2-Cl 1 O O CH₃ 773 C1 4-CH₃ H H 1 CH₃ CH₃ 2-Cl 1 O O CH₃ 774C1 4-CH₃ H H 1 CH₃ Et 2-Cl 1 O O CH₃ 775 C1 4-CH₃ H H 1 CH₃ CH₃CO 2-Cl 1O O CH₃ 776 C1 4-CH₃ H H 1 CH₃ CH₃CH₂CO 2-Cl 1 O O CH₃ 777 C1 4-CH₃ H H1 CH₃ PhCO 2-Cl 1 O O CH₃ 778 C1 4-CH₃ H H 1 CH₃ 4-Cl-PhCO 2-Cl 1 O OCH₃ 779 C1 4-CH₃ H H 1 CH₃ PhCH₂CO 2-Cl 1 O O CH₃ 780 C1 4-CH₃ H H 1 CH₃CHO 2-Cl 1 O O CH₃ 781 C1 4-CH₃ H H 1 CH₃ CH₃OCH₂ 2-Cl 1 O O CH₃ 782 C14-CH₃ H H 1 CH₃ CH₃CH(OCH₃) 2-Cl 1 O O CH₃ 783 C1 4-CH₃ H H 1 CH₃ CH₃SO₂2-Cl 1 O O CH₃ 784 C1 4-CH₃ H H 1 CH₃ PhSO₂ 2-Cl 1 O O CH₃ 785 C1 4-CH₃H H 1 CH₃ 4-CH₃-PhSO₂ 2-Cl 1 O O CH₃ 786 C1 4-CH₃ H H 1 CH₃ H 2-Cl 1 S OCH₃ 787 C1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O S CH₃

TABLE 14 788 C1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O — CH₃ 789 C1 4-CH₃ H H 1 CH₃H 2-Cl 1 O NH CH₃ 790 C1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O NCH₃ CH₃ 791 C14-CH₃ H H 1 CH₃ H 2-Cl 1 O O H 792 C1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O Et793 C1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O n-Pr 794 C1 4-CH₃ H H 1 CH₃ H 2-Cl 1O O CH₂CH═CH₂ 795 C1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH═CH₂ 796 C1 4-CH₃ HH 1 CH₃ H 2-Cl 1 O O Propargyl 797 C1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O Oethynyl 798 C1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O CF₃ 799 C1 4-CH₃ H H 1 CH₃ H2-Cl 1 O O CH₂CF₃ 800 C1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O CF₂CF₃ 801 C14-CH₃ H H 1 CH₃ H 2-Cl 1 O O CF₂CF₂H 802 C1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O OCH₂CH═CHCl 803 C1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O 3-Iodo-Propargy 804 C14-CH₃ H H 1 CH₃ H 2-Cl 1 O O c-Pr 805 C1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O OO-Hex 806 C1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O 2-CH₃-c-Pr 807 C1 — H H 1 CH₃H 2-CH₃ 1 O O CH₃ 808 C1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 809 C1 4-Et HH 1 CH₃ H 2-CH₃ 1 O O CH₃ 810 C1 4-CF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 811C1 4-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 812 C1 4-Cl H H 1 CH₃ H 2-CH₃ 1 O OCH₃ 813 C1 4-OCH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 814 C1 4-OEt H H 1 CH₃ H2-CH₃ 1 O O CH₃ 815 C1 4-OCF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 816 C1 5-CH₃ HH 1 CH₃ H 2-CH₃ 1 O O CH₃ 817 C1 5-Et H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 818 C15-CF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 819 C1 5-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃820 C1 5-Cl H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 821 C1 5-OCH₃ H H 1 CH₃ H 2-CH₃1 O O CH₃ 822 C1 5-OEt H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 823 C1 5-OCF₃ H H 1CH₃ H 2-CH₃ 1 O O CH₃ 824 C1 4,5-diCH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 825C1 4-Et-5-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 826 C1 4-CF₃-5-F H H 1 CH₃ H2-CH₃ 1 O O CH₃ 827 C1 4,5-diF H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 828 C14-Cl-5-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 829 C1 4,5-diOCH₃ H H 1 CH₃ H 2-CH₃1 O O CH₃ 830 C1 4-OEt-5-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 831 C14-OCF₃-5-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 832 C1 4-CH₃ H CH₃ 1 CH₃ H 2-CH₃1 O O CH₃ 833 C1 4-Et H CH₃ 1 CH₃ H 2-CH₃ 1 O O CH₃ 834 C1 4-CH₃ H Et 1CH₃ H 2-CH₃ 1 O O CH₃ 835 C1 4-CH₃ H I-Pr 1 CH₃ H 2-CH₃ 1 O O CH₃ 836 C14-CH₃ CH₃ Et 1 CH₃ H 2-CH₃ 1 O O CH₃ 837 C1 4-CH₃ H F 1 CH₃ H 2-CH₃ 1 OO CH₃ 838 C1 4-CH₃ F F 1 CH₃ H 2-CH₃ 1 O O CH₃ 839 C1 4-CH₃ H CF₃ 1 CH₃H 2-CH₃ 1 O O CH₃ 840 C1 4-CH₃ H c-Pr 1 CH₃ H 2-CH₃ 1 O O CH₃ 841 C14-CH₃ —CH2CH2— 1 CH₃ H 2-CH₃ 1 O O CH₃ 842 C1 4-CH₃ —CH2CH2CH2— 1 CH₃ H2-CH₃ 1 O O CH₃ 843 C1 4-CH₃ —CH2CH(CH3)— 1 CH₃ H 2-CH₃ 1 O O CH₃ 844 C14-CH₃ —CH2C(CH3)2— 1 CH₃ H 2-CH₃ 1 O O CH₃ 845 C1 4-CH₃ H H 1 H H 2-CH₃1 O O CH₃ 846 C1 4-CH₃ H H 1 Et H 2-CH₃ 1 O O CH₃ 847 C1 4-CH₃ H H 1c-Pr H 2-CH₃ 1 O O CH₃

TABLE 15 848 C1 4-CH₃ H H 1 CH═CH₂ H 2-CH₃ 1 O O CH₃ 849 C1 4-CH₃ H H 1CH₂CH═CH₂ H 2-CH₃ 1 O O CH₃ 850 C1 4-CH₃ H H 1 ethynyl H 2-CH₃ 1 O O CH₃851 C1 4-CH₃ H H 1 Propargyl H 2-CH₃ 1 O O CH₃ 852 C1 4-CH₃ H H 1 CF₃ H2-CH₃ 1 O O CH₃ 853 C1 4-CH₃ H H 1 CH═CHCl H 2-CH₃ 1 O O CH₃ 854 C14-CH₃ H H 1 3,3,2-tri-Iodo-allyl H 2-CH₃ 1 O O CH₃ 855 C1 4-CH₃ H H 13-Iodopropargyl H 2-CH₃ 1 O O CH₃ 856 C1 4-CH₃ H H 1 CN H 2-CH₃ 1 O OCH₃ 857 C1 4-CF₃ H H 1 CN H 2-CH₃ 1 O O CH₃ 858 C1 4-CH₃ H H 1 NO₂ H2-CH₃ 1 O O CH₃ 859 C1 4-CH₃ H H 1 NH₂ H 2-CH₃ 1 O O CH₃ 860 C1 4-CH₃ HH 1 NHCH₃ H 2-CH₃ 1 O O CH₃ 861 C1 4-CH₃ H H 1 N(CH₃)₂ H 2-CH₃ 1 O O CH₃862 C1 4-CH₃ H H 1 CH₃ CH₃ 2-CH₃ 1 O O CH₃ 863 C1 4-CH₃ H H 1 CH₃ Et2-CH₃ 1 O O CH₃ 864 C1 4-CH₃ H H 1 CH₃ CH₃CO 2-CH₃ 1 O O CH₃ 865 C14-CH₃ H H 1 CH₃ CH₃CH₂CO 2-CH₃ 1 O O CH₃ 866 C1 4-CH₃ H H 1 CH₃ PhCO2-CH₃ 1 O O CH₃ 867 C1 4-CH₃ H H 1 CH₃ 4-Cl-PhCO 2-CH₃ 1 O O CH₃ 868 C14-CH₃ H H 1 CH₃ PhCH₂CO 2-CH₃ 1 O O CH₃ 869 C1 4-CH₃ H H 1 CH₃ CHO 2-CH₃1 O O CH₃ 870 C1 4-CH₃ H H 1 CH₃ CH₃OCH₂ 2-CH₃ 1 O O CH₃ 871 C1 4-CH₃ HH 1 CH₃ CH₃CH(OCH₃) 2-CH₃ 1 O O CH₃ 872 C1 4-CH₃ H H 1 CH₃ CH₃SO₂ 2-CH₃1 O O CH₃ 873 C1 4-CH₃ H H 1 CH₃ PhSO₂ 2-CH₃ 1 O O CH₃ 874 C1 4-CH₃ H H1 CH₃ 4-CH₃-PhSO₂ 2-CH₃ 1 O O CH₃ 875 C1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 S OCH₃ 876 C1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O S CH₃ 877 C1 4-CH₃ H H 1 CH₃ H2-CH₃ 1 O — CH₃ 878 C1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O NH CH₃ 879 C1 4-CH₃ HH 1 CH₃ H 2-CH₃ 1 O NCH₃ CH₃ 880 C1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O H 881C1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O Et 882 C1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O On-Pr 883 C1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CH═CH₂ 884 C1 4-CH₃ H H 1CH₃ H 2-CH₃ 1 O O CH═CH₂ 885 C1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O Propargyl886 C1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O ethynyl 887 C1 4-CH₃ H H 1 CH₃ H2-CH₃ 1 O O CF₃ 888 C1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CF₃ 889 C1 4-CH₃H H 1 CH₃ H 2-CH₃ 1 O O CF₂CF₃ 890 C1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O OCF₂CF₂H 891 C1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CH═CHCl 892 C1 4-CH₃ H H1 CH₃ H 2-CH₃ 1 O O 3-Iodo-Propargyl 893 C1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 OO c-Pr 894 C1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O c-Hex 895 C1 4-CH₃ H H 1 CH₃H 2-CH₃ 1 O O 2-CH₃-c-Pr 896 C2 — H H 1 CH₃ H — 0 O O CH₃ 897 C2 — H H 1CH₃ H 2-Cl 1 O O CH₃ 898 C2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 899 C2 2-EtH H 1 CH₃ H 2-Cl 1 O O CH₃ 900 C2 2-CF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 901C2 2-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 902 C2 2-Cl H H 1 CH₃ H 2-Cl 1 O O CH₃903 C2 2-OCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 904 C2 2-OEt H H 1 CH₃ H 2-Cl 1O O CH₃ 905 C2 2-OCF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 906 C2 5-CH₃ H H 1 CH₃H 2-Cl 1 O O CH₃ 907 C2 5-Et H H 1 CH₃ H 2-Cl 1 O O CH₃ 908 C2 5-CF₃ H H1 CH₃ H 2-Cl 1 O O CH₃ 909 C2 5-F H H 1 CH₃ H 2-Cl 1 O O CH₃

TABLE 16 910 C2 5-Cl H H 1 CH₃ H 2-Cl 1 O O CH₃ 911 C2 5-OCH₃ H H 1 CH₃H 2-Cl 1 O O CH₃ 912 C2 5-OEt H H 1 CH₃ H 2-Cl 1 O O CH₃ 913 C2 5-OCF₃ HH 1 CH₃ H 2-Cl 1 O O CH₃ 914 C2 2,5-diCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 915C2 2-Et-5-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 916 C2 2-CF₃-5-F H H 1 CH₃ H2-Cl 1 O O CH₃ 917 C2 2,5-diF H H 1 CH₃ H 2-Cl 1 O O CH₃ 918 C2 2-Cl-5-FH H 1 CH₃ H 2-Cl 1 O O CH₃ 919 C2 2,5-diOCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃920 C2 2-OEt-5-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 921 C2 2-OCF₃-5-F H H 1CH₃ H 2-Cl 1 O O CH₃ 922 C2 2-CH₃ H CH₃ 1 CH₃ H 2-Cl 1 O O CH₃ 923 C22-Et H CH₃ 1 CH₃ H 2-Cl 1 O O CH₃ 924 C2 2-CH₃ H Et 1 CH₃ H 2-Cl 1 O OCH₃ 925 C2 2-CH₃ H i-Pr 1 CH₃ H 2-Cl 1 O O CH₃ 926 C2 2-CH₃ CH₃ Et 1 CH₃H 2-Cl 1 O O CH₃ 927 C2 2-CH₃ H F 1 CH₃ H 2-Cl 1 O O CH₃ 928 C2 2-CH₃ FF 1 CH₃ H 2-Cl 1 O O CH₃ 929 C2 2-CH₃ H CF₃ 1 CH₃ H 2-Cl 1 O O CH₃ 930C2 2-CH₃ H c-Pr 1 CH₃ H 2-Cl 1 O O CH₃ 931 C2 2-CH₃ —CH2CH2— 1 CH₃ H2-Cl 1 O O CH₃ 932 C2 2-CH₃ —CH2CH2CH2— 1 CH₃ H 2-Cl 1 O O CH₃ 933 C22-CH₃ —CH2CH(CH3)— 1 CH₃ H 2-Cl 1 O O CH₃ 934 C2 2-CH₃ —CH2C(CH3)2— 1CH₃ H 2-Cl 1 O O CH₃ 935 C2 2-CH₃ H H 1 H H 2-Cl 1 O O CH₃ 936 C2 2-CH₃H H 1 Et H 2-Cl 1 O O CH₃ 937 C2 2-CH₃ H H 1 c-Pr H 2-Cl 1 O O CH₃ 938C2 2-CH₃ H H 1 CH═CH₂ H 2-Cl 1 O O CH₃ 939 C2 2-CH₃ H H 1 CH₂CH═CH₂ H2-Cl 1 O O CH₃ 940 C2 2-CH₃ H H 1 ethynyl H 2-Cl 1 O O CH₃ 941 C2 2-CH₃H H 1 Propargyl H 2-Cl 1 O O CH₃ 942 C2 2-CH₃ H H 1 CF₃ H 2-Cl 1 O O CH₃943 C2 2-CH₃ H H 1 CH═CHCl H 2-Cl 1 O O CH₃ 944 C2 2-CH₃ H H 13,3,2-tri-Iodo-allyl H 2-Cl 1 O O CH₃ 945 C2 2-CH₃ H H 1 3-IodopropargylH 2-Cl 1 O O CH₃ 946 C2 2-CH₃ H H 1 CN H 2-Cl 1 O O CH₃ 947 C2 2-CF₃ H H1 CN H 2-Cl 1 O O CH₃ 948 C2 2-CH₃ H H 1 NO₂ H 2-Cl 1 O O CH₃ 949 C22-CH₃ H H 1 NH₂ H 2-Cl 1 O O CH₃ 950 C2 2-CH₃ H H 1 NHCH₃ H 2-Cl 1 O OCH₃ 951 C2 2-CH₃ H H 1 N(CH₃)₂ H 2-Cl 1 O O CH₃ 952 C2 2-CH₃ H H 1 CH₃CH₃ 2-Cl 1 O O CH₃ 953 C2 2-CH₃ H H 1 CH₃ Et 2-Cl 1 O O CH₃ 954 C2 2-CH₃H H 1 CH₃ CH₃CO 2-Cl 1 O O CH₃ 955 C2 2-CH₃ H H 1 CH₃ CH₃CH₂CO 2-Cl 1 OO CH₃ 956 C2 2-CH₃ H H 1 CH₃ PhCO 2-Cl 1 O O CH₃ 957 C2 2-CH₃ H H 1 CH₃4-Cl-PhCO 2-Cl 1 O O CH₃ 958 C2 2-CH₃ H H 1 CH₃ PhCH₂CO 2-Cl 1 O O CH₃959 C2 2-CH₃ H H 1 CH₃ CHO 2-Cl 1 O O CH₃ 960 C2 2-CH₃ H H 1 CH₃ CH₃OCH₂2-Cl 1 O O CH₃ 961 C2 2-CH₃ H H 1 CH₃ CH₃CH(OCH₃) 2-Cl 1 O O CH₃ 962 C22-CH₃ H H 1 CH₃ CH₃SO₂ 2-Cl 1 O O CH₃ 963 C2 2-CH₃ H H 1 CH₃ PhSO₂ 2-Cl1 O O CH₃ 964 C2 2-CH₃ H H 1 CH₃ 4-CH₃-PhSO₂ 2-Cl 1 O O CH₃ 965 C2 2-CH₃H H 1 CH₃ H 2-Cl 1 S O CH₃ 966 C2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O S CH₃ 967C2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O — CH₃ 968 C2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O NHCH₃ 969 C2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O NCH₃ CH₃ 970 C2 2-CH₃ H H 1 CH₃ H2-Cl 1 O O H 971 C2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O Et

TABLE 17 972 C2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O n-Pr 973 C2 2-CH₃ H H 1 CH₃H 2-Cl 1 O O CH₂CH═CH₂ 974 C2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH═CH₂ 975 C22-CH₃ H H 1 CH₃ H 2-Cl 1 O O Propargyl 976 C2 2-CH₃ H H 1 CH₃ H 2-Cl 1 OO ethynyl 977 C2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O CF₃ 978 C2 2-CH₃ H H 1 CH₃H 2-Cl 1 O O CH₂CF₃ 979 C2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O CF₂CF₃ 980 C22-CH₃ H H 1 CH₃ H 2-Cl 1 O O CF₂CF₂H 981 C2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O OCH₂CH═CHCl 982 C2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O 3-Iodo-Propargyl 983 C22-CH₃ H H 1 CH₃ H 2-Cl 1 O O c-Pr 984 C2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O Oc-Hex 985 C2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O 2-CH₃-c-Pr 986 C2 — H H 1 CH₃H 2-CH₃ 1 O O CH₃ 987 C2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 988 C2 2-Et HH 1 CH₃ H 2-CH₃ 1 O O CH₃ 989 C2 2-CF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 990C2 2-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 991 C2 2-Cl H H 1 CH₃ H 2-CH₃ 1 O OCH₃ 992 C2 2-OCH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 993 C2 2-OEt H H 1 CH₃ H2-CH₃ 1 O O CH₃ 994 C2 2-OCF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 995 C2 5-CH₃ HH 1 CH₃ H 2-CH₃ 1 O O CH₃ 996 C2 5-Et H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 997 C25-CF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 998 C2 5-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃999 C2 5-Cl H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1000 C2 5-OCH₃ H H 1 CH₃ H 2-CH₃1 O O CH₃ 1001 C2 5-OEt H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1002 C2 5-OCF₃ H H 1CH₃ H 2-CH₃ 1 O O CH₃ 1003 C2 2,5-diCH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1004C2 2-Et-5-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1005 C2 2-CF₃-5-F H H 1 CH₃ H2-CH₃ 1 O O CH₃ 1006 C2 2,5-diF H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1007 C22-Cl-5-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1008 C2 2,5-diOCH₃ H H 1 CH₃ H2-CH₃ 1 O O CH₃ 1009 C2 2-OEt-5-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1010 C22-OCF₃-5-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1011 C2 2-CH₃ H CH₃ 1 CH₃ H 2-CH₃1 O O CH₃ 1012 C2 2-Et H CH₃ 1 CH₃ H 2-CH₃ 1 O O CH₃ 1013 C2 2-CH₃ H Et1 CH₃ H 2-CH₃ 1 O O CH₃ 1014 C2 2-CH₃ H i-Pr 1 CH₃ H 2-CH₃ 1 O O CH₃1015 C2 2-CH₃ CH₃ Et 1 CH₃ H 2-CH₃ 1 O O CH₃ 1016 C2 2-CH₃ H F 1 CH₃ H2-CH₃ 1 O O CH₃ 1017 C2 2-CH₃ F F 1 CH₃ H 2-CH₃ 1 O O CH₃ 1018 C2 2-CH₃H CF₃ 1 CH₃ H 2-CH₃ 1 O O CH₃ 1019 C2 2-CH₃ H c-Pr 1 CH₃ H 2-CH₃ 1 O OCH₃ 1020 C2 2-CH₃ —CH2CH2— 1 CH₃ H 2-CH₃ 1 O O CH₃ 1021 C2 2-CH₃—CH2CH2CH_(2—) 1 CH₃ H 2-CH₃ 1 O O CH₃ 1022 C2 2-CH₃ —CH2CH(CH3)— 1 CH₃H 2-CH₃ 1 O O CH₃ 1023 C2 2-CH₃ —CH2C(CH3)2— 1 CH₃ H 2-CH₃ 1 O O CH₃1024 C2 2-CH₃ H H 1 H H 2-CH₃ 1 O O CH₃ 1025 C2 2-CH₃ H H 1 Et H 2-CH₃ 1O O CH₃ 1026 C2 2-CH₃ H H 1 c-Pr H 2-CH₃ 1 O O CH₃ 1027 C2 2-CH₃ H H 1CH═CH₂ H 2-CH₃ 1 O O CH₃ 1028 C2 2-CH₃ H H 1 CH₂CH═CH₂ H 2-CH₃ 1 O O CH₃1029 C2 2-CH₃ H H 1 ethynyl H 2-CH₃ 1 O O CH₃ 1030 C2 2-CH₃ H H 1Propargyl H 2-CH₃ 1 O O CH₃ 1031 C2 2-CH₃ H H 1 CF₃ H 2-CH₃ 1 O O CH₃1032 C2 2-CH₃ H H 1 CH═CHCl H 2-CH₃ 1 O O CH₃ 1033 C2 2-CH₃ H H 13,3,2-tri-Iodo-allyl H 2-CH₃ 1 O O CH₃

TABLE 18 1034 C2 2-CH₃ H H 1 3-Iodopropargyl H 2-CH₃ 1 O O CH₃ 1035 C22-CH₃ H H 1 CN H 2-CH₃ 1 O O CH₃ 1036 C2 2-CF₃ H H 1 CN H 2-CH₃ 1 O OCH₃ 1037 C2 2-CH₃ H H 1 NO₂ H 2-CH₃ 1 O O CH₃ 1038 C2 2-CH₃ H H 1 NH₂ H2-CH₃ 1 O O CH₃ 1039 C2 2-CH₃ H H 1 NHCH₃ H 2-CH₃ 1 O O CH₃ 1040 C22-CH₃ H H 1 N(CH₃)₂ H 2-CH₃ 1 O O CH₃ 1041 C2 2-CH₃ H H 1 CH₃ CH₃ 2-CH₃1 O O CH₃ 1042 C2 2-CH₃ H H 1 CH₃ Et 2-CH₃ 1 O O CH₃ 1043 C2 2-CH₃ H H 1CH₃ CH₃CO 2-CH₃ 1 O O CH₃ 1044 C2 2-CH₃ H H 1 CH₃ CH₃CH₂CO 2-CH₃ 1 O OCH₃ 1045 C2 2-CH₃ H H 1 CH₃ PhCO 2-CH₃ 1 O O CH₃ 1046 C2 2-CH₃ H H 1 CH₃4-Cl-PhCO 2-CH₃ 1 O O CH₃ 1047 C2 2-CH₃ H H 1 CH₃ PhCH₂CO 2-CH₃ 1 O OCH₃ 1048 C2 2-CH₃ H H 1 CH₃ CHO 2-CH₃ 1 O O CH₃ 1049 C2 2-CH₃ H H 1 CH₃CH₃OCH₂ 2-CH₃ 1 O O CH₃ 1050 C2 2-CH₃ H H 1 CH₃ CH₃CH(OCH₃) 2-CH₃ 1 O OCH₃ 1051 C2 2-CH₃ H H 1 CH₃ CH₃SO₂ 2-CH₃ 1 O O CH₃ 1052 C2 2-CH₃ H H 1CH₃ PhSO₂ 2-CH₃ 1 O O CH₃ 1053 C2 2-CH₃ H H 1 CH₃ 4-CH₃-PhSO₂ 2-CH₃ 1 OO CH₃ 1054 C2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 S O CH₃ 1055 C2 2-CH₃ H H 1 CH₃H 2-CH₃ 1 O S CH₃ 1056 C2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O — CH₃ 1057 C22-CH₃ H H 1 CH₃ H 2-CH₃ 1 O NH CH₃ 1058 C2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 ONCH₃ CH₃ 1059 C2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O H 1060 C2 2-CH₃ H H 1 CH₃H 2-CH₃ 1 O O Et 1061 C2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O n-Pr 1062 C22-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CH═CH₂ 1063 C2 2-CH₃ H H 1 CH₃ H 2-CH₃1 O O CH═CH₂ 1064 C2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O Propargyl 1065 C22-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O ethynyl 1066 C2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1O O CF₃ 1067 C2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CF₃ 1068 C2 2-CH₃ H H 1CH₃ H 2-CH₃ 1 O O CF₂CF₃ 1069 C2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CF₂CF₂H1070 C2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CH═CHCl 1071 C2 2-CH₃ H H 1 CH₃H 2-CH₃ 1 O O 3-Iodo-propargy 1072 C2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O c-Pr1073 C2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O c-Hex 1074 C2 2-CH₃ H H 1 CH₃ H2-CH₃ 1 O O 2-CH₃-c-Pr 1075 D1 — H H 1 CH₃ H — 0 O O CH₃ 1076 D1 — H H 1CH₃ H 2-Cl 1 O O CH₃ 1077 D1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1078 D14-Et H H 1 CH₃ H 2-Cl 1 O O CH₃ 1079 D1 4-CF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃1080 D1 4-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 1081 D1 4-Cl H H 1 CH₃ H 2-Cl 1 OO CH₃ 1082 D1 4-OCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1083 D1 4-OEt H H 1 CH₃H 2-Cl 1 O O CH₃ 1084 D1 4-OCF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1085 D1 5-CH₃H H 1 CH₃ H 2-Cl 1 O O CH₃ 1086 D1 5-Et H H 1 CH₃ H 2-Cl 1 O O CH₃ 1087D1 5-CF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1088 D1 5-F H H 1 CH₃ H 2-Cl 1 O OCH₃ 1089 D1 5-Cl H H 1 CH₃ H 2-Cl 1 O O CH₃ 1090 D1 5-OCH₃ H H 1 CH₃ H2-Cl 1 O O CH₃ 1091 D1 5-OEt H H 1 CH₃ H 2-Cl 1 O O CH₃ 1092 D1 5-OCF₃ HH 1 CH₃ H 2-Cl 1 O O CH₃ 1093 D1 4,5-diCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃1094 D1 4-Et-5-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1095 D1 4-CF₃-5-F H H 1CH₃ H 2-Cl 1 O O CH₃

TABLE 19 1096 D1 4,5-diF H H 1 CH₃ H 2-Cl 1 O O CH₃ 1097 D1 4-Cl-5-F H H1 CH₃ H 2-Cl 1 O O CH₃ 1098 D1 4,5-diOCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃1099 D1 4-OEt-5-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1100 D1 4-OCF₃-5-F H H 1CH₃ H 2-Cl 1 O O CH₃ 1101 D1 4-CH₃ H CH₃ 1 CH₃ H 2-Cl 1 O O CH₃ 1102 D14-Et H CH₃ 1 CH₃ H 2-Cl 1 O O CH₃ 1103 D1 4-CH₃ H Et 1 CH₃ H 2-Cl 1 O OCH₃ 1104 D1 4-CH₃ H i-Pr 1 CH₃ H 2-Cl 1 O O CH₃ 1105 D1 4-CH₃ CH₃ Et 1CH₃ H 2-Cl 1 O O CH₃ 1106 D1 4-CH₃ H F 1 CH₃ H 2-Cl 1 O O CH₃ 1107 D14-CH₃ F F 1 CH₃ H 2-Cl 1 O O CH₃ 1108 D1 4-CH₃ H CF₃ 1 CH₃ H 2-Cl 1 O OCH₃ 1109 D1 4-CH₃ H c-Pr 1 CH₃ H 2-Cl 1 O O CH₃ 1110 D1 4-CH₃ —CH2CH2— 1CH₃ H 2-Cl 1 O O CH₃ 1111 D1 4-CH₃ —CH2CH2CH2— 1 CH₃ H 2-Cl 1 O O CH₃1112 D1 4-CH₃ —CH2CH(CH3)— 1 CH₃ H 2-Cl 1 O O CH₃ 1113 D1 4-CH₃—CH2C(CH3)2— 1 CH₃ H 2-Cl 1 O O CH₃ 1114 D1 4-CH₃ H H 1 H H 2-Cl 1 O OCH₃ 1115 D1 4-CH₃ H H 1 Et H 2-Cl 1 O O CH₃ 1116 D1 4-CH₃ H H 1 c-Pr H2-Cl 1 O O CH₃ 1117 D1 4-CH₃ H H 1 CH═CH₂ H 2-Cl 1 O O CH₃ 1118 D1 4-CH₃H H 1 CH₂CH═CH₂ H 2-Cl 1 O O CH₃ 1119 D1 4-CH₃ H H 1 ethynyl H 2-Cl 1 OO CH₃ 1120 D1 4-CH₃ H H 1 Propargyl H 2-Cl 1 O O CH₃ 1121 D1 4-CH₃ H H 1CF₃ H 2-Cl 1 O O CH₃ 1122 D1 4-CH₃ H H 1 CH═CHCl H 2-Cl 1 O O CH₃ 1123D1 4-CH₃ H H 1 3,3,2-tri-Iodo-allyl H 2-Cl 1 O O CH₃ 1124 D1 4-CH₃ H H 13-Iodopropargyl H 2-Cl 1 O O CH₃ 1125 D1 4-CH₃ H H 1 CN H 2-Cl 1 O O CH₃1126 D1 4-CF₃ H H 1 CN H 2-Cl 1 O O CH₃ 1127 D1 4-CH₃ H H 1 NO₂ H 2-Cl 1O O CH₃ 1128 D1 4-CH₃ H H 1 NH₂ H 2-Cl 1 O O CH₃ 1129 D1 4-CH₃ H H 1NHCH₃ H 2-Cl 1 O O CH₃ 1130 D1 4-CH₃ H H 1 N(CH₃)₂ H 2-Cl 1 O O CH₃ 1131D1 4-CH₃ H H 1 CH₃ CH₃ 2-Cl 1 O O CH₃ 1132 D1 4-CH₃ H H 1 CH₃ Et 2-Cl 1O O CH₃ 1133 D1 4-CH₃ H H 1 CH₃ CH₃CO 2-Cl 1 O O CH₃ 1134 D1 4-CH₃ H H 1CH₃ CH₃CH₂CO 2-Cl 1 O O CH₃ 1135 D1 4-CH₃ H H 1 CH₃ PhCO 2-Cl 1 O O CH₃1136 D1 4-CH₃ H H 1 CH₃ 4-Cl-PhCO 2-Cl 1 O O CH₃ 1137 D1 4-CH₃ H H 1 CH₃PhCH₂CO 2-Cl 1 O O CH₃ 1138 D1 4-CH₃ H H 1 CH₃ CHO 2-Cl 1 O O CH₃ 1139D1 4-CH₃ H H 1 CH₃ CH₃OCH₂ 2-Cl 1 O O CH₃ 1140 D1 4-CH₃ H H 1 CH₃CH₃CH(OCH₃) 2-Cl 1 O O CH₃ 1141 D1 4-CH₃ H H 1 CH₃ CH₃SO₂ 2-Cl 1 O O CH₃1142 D1 4-CH₃ H H 1 CH₃ PhSO₂ 2-Cl 1 O O CH₃ 1143 D1 4-CH₃ H H 1 CH₃4-CH₃PhSO₂ 2-Cl 1 O O CH₃ 1144 D1 4-CH₃ H H 1 CH₃ H 2-Cl 1 S O CH₃ 1145D1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O S CH₃ 1146 D1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O —CH₃ 1147 D1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O NH CH₃ 1148 D1 4-CH₃ H H 1 CH₃ H2-Cl 1 O NCH₃ CH₃ 1149 D1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O H 1150 D1 4-CH₃ HH 1 CH₃ H 2-Cl 1 O O Et 1151 D1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O n-Pr 1152D1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₂CH═CH₂ 1153 D1 4-CH₃ H H 1 CH₃ H 2-Cl1 O O CH═CH₂ 1154 D1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O Propargyl

TABLE 20 1155 D1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O ethynyl 1156 D1 4-CH₃ H H1 CH₃ H 2-Cl 1 O O CF₃ 1157 D1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₂CF₃ 1158D1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O CF₂CF₃ 1159 D1 4-CH₃ H H 1 CH₃ H 2-Cl 1O O CF₂CF₂H 1160 D1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₂CH═CHCl 1161 D14-CH₃ H H 1 CH₃ H 2-Cl 1 O O 3-Iodo-propargyl 1162 D1 4-CH₃ H H 1 CH₃ H2-Cl 1 O O c-Pr 1163 D1 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O c-Hex 1164 D1 4-CH₃H H 1 CH₃ H 2-Cl 1 O O 2-CH₃-c-Pr 1165 D1 — H H 1 CH₃ H 2-CH₃ 1 O O CH₃1166 D1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1167 D1 4-Et H H 1 CH₃ H 2-CH₃1 O O CH₃ 1168 D1 4-CF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1169 D1 4-F H H 1CH₃ H 2-CH₃ 1 O O CH₃ 1170 D1 4-Cl H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1171 D14-OCH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1172 D1 4-OEt H H 1 CH₃ H 2-CH₃ 1 O OCH₃ 1173 D1 4-OCF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1174 D1 5-CH₃ H H 1 CH₃ H2-CH₃ 1 O O CH₃ 1175 D1 5-Et H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1176 D1 5-CF₃ HH 1 CH₃ H 2-CH₃ 1 O O CH₃ 1177 D1 5-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1178D1 5-Cl H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1179 D1 5-OCH₃ H H 1 CH₃ H 2-CH₃ 1 OO CH₃ 1180 D1 5-OEt H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1181 D1 5-OCF₃ H H 1 CH₃H 2-CH₃ 1 O O CH₃ 1182 D1 4,5-diCH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1183 D14-Et-5-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1184 D1 4-CF₃-5-F H H 1 CH₃ H2-CH₃ 1 O O CH₃ 1185 D1 4,5-diF H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1186 D14-Cl-5-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1187 D1 4,5-diOCH₃ H H 1 CH₃ H2-CH₃ 1 O O CH₃ 1188 D1 4-OEt-5-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1189 D14-OCF₃-5-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1190 D1 4-CH₃ H CH₃ 1 CH₃ H 2-CH₃1 O O CH₃ 1191 D1 4-Et H CH₃ 1 CH₃ H 2-CH₃ 1 O O CH₃ 1192 D1 4-CH₃ H Et1 CH₃ H 2-CH₃ 1 O O CH₃ 1193 D1 4-CH₃ H i-Pr 1 CH₃ H 2-CH₃ 1 O O CH₃1194 D1 4-CH₃ CH₃ Et 1 CH₃ H 2-CH₃ 1 O O CH₃ 1195 D1 4-CH₃ H F 1 CH₃ H2-CH₃ 1 O O CH₃ 1196 D1 4-CH₃ F F 1 CH₃ H 2-CH₃ 1 O O CH₃ 1197 D1 4-CH₃H CF₃ 1 CH₃ H 2-CH₃ 1 O O CH₃ 1198 D1 4-CH₃ H c-Pr 1 CH₃ H 2-CH₃ 1 O OCH₃ 1199 D1 4-CH₃ —CH2CH2— 1 CH₃ H 2-CH₃ 1 O O CH₃ 1200 D1 4-CH₃—CH2CH2CH2— 1 CH₃ H 2-CH₃ 1 O O CH₃ 1201 D1 4-CH₃ —CH2CH(CH3)— 1 CH₃ H2-CH₃ 1 O O CH₃ 1202 D1 4-CH₃ —CH2C(CH3)2— 1 CH₃ H 2-CH₃ 1 O O CH₃ 1203D1 4-CH₃ H H 1 H H 2-CH₃ 1 O O CH₃ 1204 D1 4-CH₃ H H 1 Et H 2-CH₃ 1 O OCH₃ 1205 D1 4-CH₃ H H 1 c-Pr H 2-CH₃ 1 O O CH₃ 1206 D1 4-CH₃ H H 1CH═CH₂ H 2-CH₃ 1 O O CH₃ 1207 D1 4-CH₃ H H 1 CH₂OH═CH₂ H 2-CH₃ 1 O O CH₃1208 D1 4-CH₃ H H 1 ethynyl H 2-CH₃ 1 O O CH₃ 1209 D1 4-CH₃ H H 1Propargyl H 2-CH₃ 1 O O CH₃ 1210 D1 4-CH₃ H H 1 CF₃ H 2-CH₃ 1 O O CH₃1211 D1 4-CH₃ H H 1 CH═CHCl H 2-CH₃ 1 O O CH₃ 1212 D1 4-CH₃ H H 13,3,2-tri-Iodo-allyl H 2-CH₃ 1 O O CH₃ 1213 D1 4-CH₃ H H 13-Iodopropargyl H 2-CH₃ 1 O O CH₃ 1214 D1 4-CH₃ H H 1 CN H 2-CH₃ 1 O OCH₃

TABLE 21 1215 D1 4-CF₃ H H 1 CN H 2-CH₃ 1 O O CH₃ 1216 D1 4-CH₃ H H 1NO₂ H 2-CH₃ 1 O O CH₃ 1217 D1 4-CH₃ H H 1 NH₂ H 2-CH₃ 1 O O CH₃ 1218 D14-CH₃ H H 1 NHCH₃ H 2-CH₃ 1 O O CH₃ 1219 D1 4-CH₃ H H 1 N(CH₃)₂ H 2-CH₃1 O O CH₃ 1220 D1 4-CH₃ H H 1 CH₃ CH₃ 2-CH₃ 1 O O CH₃ 1221 D1 4-CH₃ H H1 CH₃ Et 2-CH₃ 1 O O CH₃ 1222 D1 4-CH₃ H H 1 CH₃ CH₃CO 2-CH₃ 1 O O CH₃1223 D1 4-CH₃ H H 1 CH₃ CH₃CH₂CO 2-CH₃ 1 O O CH₃ 1224 D1 4-CH₃ H H 1 CH₃PhCO 2-CH₃ 1 O O CH₃ 1225 D1 4-CH₃ H H 1 CH₃ 4-Cl-PhCO 2-CH₃ 1 O O CH₃1226 D1 4-CH₃ H H 1 CH₃ PhCH₂CO 2-CH₃ 1 O O CH₃ 1227 D1 4-CH₃ H H 1 CH₃CHO 2-CH₃ 1 O O CH₃ 1228 D1 4-CH₃ H H 1 CH₃ CH₃OCH₂ 2-CH₃ 1 O O CH₃ 1229D1 4-CH₃ H H 1 CH₃ CH₃CH(OCH₃) 2-CH₃ 1 O O CH₃ 1230 D1 4-CH₃ H H 1 CH₃CH₃SO₂ 2-CH₃ 1 O O CH₃ 1231 D1 4-CH₃ H H 1 CH₃ PhSO₂ 2-CH₃ 1 O O CH₃1232 D1 4-CH₃ H H 1 CH₃ 4-CH₃-PhSO₂ 2-CH₃ 1 O O CH₃ 1233 D1 4-CH₃ H H 1CH₃ H 2-CH₃ 1 S O CH₃ 1234 D1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O S CH₃ 1235 D14-CH₃ H H 1 CH₃ H 2-CH₃ 1 O — CH₃ 1236 D1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O NHCH₃ 1237 D1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O NCH₃ CH₃ 1238 D1 4-CH₃ H H 1 CH₃H 2-CH₃ 1 O O H 1239 D1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O Et 1240 D1 4-CH₃ HH 1 CH₃ H 2-CH₃ 1 O O n-Pr 1241 D1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O OCH₂CH═CH₂ 1242 D1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH═CH₂ 1243 D1 4-CH₃ H H1 CH₃ H 2-CH₃ 1 O O Propargyl 1244 D1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O Oethynyl 1245 D1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CF₃ 1246 D1 4-CH₃ H H 1CH₃ H 2-CH₃ 1 O O CH₂CF₃ 1247 D1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CF₂CF₃1248 D1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CF₂CF₂H 1249 D1 4-CH₃ H H 1 CH₃ H2-CH₃ 1 O O CH₂CH═CHCl 1250 D1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O3-Iodo-propargyl 1251 D1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O c-Pr 1252 D14-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O c-Hex 1253 D1 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 OO 2-CH₃-c-Pr 1254 D2 — H H 1 CH₃ H — 0 O O CH₃ 1255 D2 — H H 1 CH₃ H2-Cl 1 O O CH₃ 1256 D2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1257 D2 2-Et H H1 CH₃ H 2-Cl 1 O O CH₃ 1258 D2 2-CF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1259 D22-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 1260 D2 2-Cl H H 1 CH₃ H 2-Cl 1 O O CH₃1261 D2 2-OCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1262 D2 2-OEt H H 1 CH₃ H 2-Cl1 O O CH₃ 1263 D2 2-OCF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1264 D2 5-CH₃ H H 1CH₃ H 2-Cl 1 O O CH₃ 1265 D2 5-Et H H 1 CH₃ H 2-Cl 1 O O CH₃ 1266 D25-CF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1267 D2 5-F H H 1 CH₃ H 2-Cl 1 O O CH₃1268 D2 5-Cl H H 1 CH₃ H 2-Cl 1 O O CH₃ 1269 D2 5-OCH₃ H H 1 CH₃ H 2-Cl1 O O CH₃ 1270 D2 5-OEt H H 1 CH₃ H 2-Cl 1 O O CH₃ 1271 D2 5-OCF₃ H H 1CH₃ H 2-Cl 1 O O CH₃ 1272 D2 2,5-diCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1273D2 2-Et-5-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1274 D2 2-CF₃-5-F H H 1 CH₃ H2-Cl 1 O O CH₃ 1275 D2 2,5-diF H H 1 CH₃ H 2-Cl 1 O O CH₃ 1276 D22-Cl-5-F H H 1 CH₃ H 2-Cl 1 O O CH₃

TABLE 22 1277 D2 2,5-diOCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1278 D22-OEt-5-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1279 D2 2-OCF₃-5-F H H 1 CH₃ H2-Cl 1 O O CH₃ 1280 D2 2-CH₃ H CH₃ 1 CH₃ H 2-Cl 1 O O CH₃ 1281 D2 2-Et HCH₃ 1 CH₃ H 2-Cl 1 O O CH₃ 1282 D2 2-CH₃ H Et 1 CH₃ H 2-Cl 1 O O CH₃1283 D2 2-CH₃ H i-Pr 1 CH₃ H 2-Cl 1 O O CH₃ 1284 D2 2-CH₃ CH₃ Et 1 CH₃ H2-Cl 1 O O CH₃ 1285 D2 2-CH₃ H F 1 CH₃ H 2-Cl 1 O O CH₃ 1286 D2 2-CH₃ FF 1 CH₃ H 2-Cl 1 O O CH₃ 1287 D2 2-CH₃ H CF₃ 1 CH₃ H 2-Cl 1 O O CH₃ 1288D2 2-CH₃ H c-Pr 1 CH₃ H 2-Cl 1 O O CH₃ 1289 D2 2-CH₃ —CH2CH2— 1 CH₃ H2-Cl 1 O O CH₃ 1290 D2 2-CH₃ —CH2CH2CH2— 1 CH₃ H 2-Cl 1 O O CH₃ 1291 D22-CH₃ —CH2CH(CH3)— 1 CH₃ H 2-Cl 1 O O CH₃ 1292 D2 2-CH₃ —CH2C(CH3)2— 1CH₃ H 2-Cl 1 O O CH₃ 1293 D2 2-CH₃ H H 1 H H 2-Cl 1 O O CH₃ 1294 D22-CH₃ H H 1 Et H 2-Cl 1 O O CH₃ 1295 D2 2-CH₃ H H 1 c-Pr H 2-Cl 1 O OCH₃ 1296 D2 2-CH₃ H H 1 CH═CH₂ H 2-Cl 1 O O CH₃ 1297 D2 2-CH₃ H H 1CH₂CH═CH₂ H 2-Cl 1 O O CH₃ 1298 D2 2-CH₃ H H 1 ethynyl H 2-Cl 1 O O CH₃1299 D2 2-CH₃ H H 1 Propargyl H 2-Cl 1 O O CH₃ 1300 D2 2-CH₃ H H 1 CF₃ H2-Cl 1 O O CH₃ 1301 D2 2-CH₃ H H 1 CH═CHCl H 2-Cl 1 O O CH₃ 1302 D22-CH₃ H H 1 3,3,2-tri-Iodo-allyl H 2-Cl 1 O O CH₃ 1303 D2 2-CH₃ H H 13-Iodopropargyl H 2-Cl 1 O O CH₃ 1304 D2 2-CH₃ H H 1 CN H 2-Cl 1 O O CH₃1305 D2 2-CF₃ H H 1 CN H 2-Cl 1 O O CH₃ 1306 D2 2-CH₃ H H 1 NO₂ H 2-Cl 1O O CH₃ 1307 D2 2-CH₃ H H 1 NH₂ H 2-Cl 1 O O CH₃ 1308 D2 2-CH₃ H H 1NHCH₃ H 2-Cl 1 O O CH₃ 1309 D2 2-CH₃ H H 1 N(CH₃)₂ H 2-Cl 1 O O CH₃ 1310D2 2-CH₃ H H 1 CH₃ CH₃ 2-Cl 1 O O CH₃ 1311 D2 2-CH₃ H H 1 CH₃ Et 2-Cl 1O O CH₃ 1312 D2 2-CH₃ H H 1 CH₃ CH₃CO 2-Cl 1 O O CH₃ 1313 D2 2-CH₃ H H 1CH₃ CH₃CH₂CO 2-Cl 1 O O CH₃ 1314 D2 2-CH₃ H H 1 CH₃ PhCO 2-Cl 1 O O CH₃1315 D2 2-CH₃ H H 1 CH₃ 4-Cl-PhCO 2-Cl 1 O O CH₃ 1316 D2 2-CH₃ H H 1 CH₃PhCH₂CO 2-Cl 1 O O CH₃ 1317 D2 2-CH₃ H H 1 CH₃ CHO 2-Cl 1 O O CH₃ 1318D2 2-CH₃ H H 1 CH₃ CH₃OCH₂ 2-Cl 1 O O CH₃ 1319 D2 2-CH₃ H H 1 CH₃CH₃CH(OCH₃) 2-Cl 1 O O CH₃ 1320 D2 2-CH₃ H H 1 CH₃ CH₃SO₂ 2-Cl 1 O O CH₃1321 D2 2-CH₃ H H 1 CH₃ PhSO₂ 2-Cl 1 O O CH₃ 1322 D2 2-CH₃ H H 1 CH₃4-CH₃-PhSO₂ 2-Cl 1 O O CH₃ 1323 D2 2-CH₃ H H 1 CH₃ H 2-Cl 1 S O CH₃ 1324D2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O S CH₃ 1325 D2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O —CH₃ 1326 D2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O NH CH₃ 1327 D2 2-CH₃ H H 1 CH₃ H2-Cl 1 O NCH₃ CH₃ 1328 D2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O H 1329 D2 2-CH₃ HH 1 CH₃ H 2-Cl 1 O O Et 1330 D2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O n-Pr 1331D2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₂CH═CH₂ 1332 D2 2-CH₃ H H 1 CH₃ H 2-Cl1 O O CH═CH₂ 1333 D2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O Propargyl 1334 D22-CH₃ H H 1 CH₃ H 2-Cl 1 O O ethynyl 1335 D2 2-CH₃ H H 1 CH₃ H 2-Cl 1 OO CF₃ 1336 D2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₂CF₃ 1337 D2 2-CH₃ H H 1CH₃ H 2-Cl 1 O O CF₂CF₃ 1338 D2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O CF₂CF₂H

TABLE 23 1339 D2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₂CH═CHCl 1340 D2 2-CH₃ HH 1 CH₃ H 2-Cl 1 O O 3-Iodo-propargyl 1341 D2 2-CH₃ H H 1 CH₃ H 2-Cl 1 OO c-Pr 1342 D2 2-CH₃ H H 1 CH₃ H 2-Cl 1 O O c-Hex 1343 D2 2-CH₃ H H 1CH₃ H 2-Cl 1 O O 2-CH₃-c-Pr 1344 D2 — H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1345D2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1346 D2 2-Et H H 1 CH₃ H 2-CH₃ 1 OO CH₃ 1347 D2 2-CF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1348 D2 2-F H H 1 CH₃ H2-CH₃ 1 O O CH₃ 1349 D2 2-Cl H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1350 D2 2-OCH₃H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1351 D2 2-OEt H H 1 CH₃ H 2-CH₃ 1 O O CH₃1352 D2 2-OCF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1353 D2 5-CH₃ H H 1 CH₃ H2-CH₃ 1 O O CH₃ 1354 D2 5-Et H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1355 D2 5-CF₃ HH 1 CH₃ H 2-CH₃ 1 O O CH₃ 1356 D2 5-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1357D2 5-Cl H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1358 D2 5-OCH₃ H H 1 CH₃ H 2-CH₃ 1 OO CH₃ 1359 D2 5-OEt H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1360 D2 5-OCF₃ H H 1 CH₃H 2-CH₃ 1 O O CH₃ 1361 D2 2,5-diCH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1362 D22-Et-5-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1363 D2 2-CF₃-5-F H H 1 CH₃ H2-CH₃ 1 O O CH₃ 1364 D2 2,5-diF H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1365 D22-Cl-5-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1366 D2 2,5-diOCH₃ H H 1 CH₃ H2-CH₃ 1 O O CH₃ 1367 D2 2-OEt-5-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1368 D22-OCF₃-5-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1369 D2 2-CH₃ H CH₃ 1 CH₃ H 2-CH₃1 O O CH₃ 1370 D2 2-Et H CH₃ 1 CH₃ H 2-CH₃ 1 O O CH₃ 1371 D2 2-CH₃ H Et1 CH₃ H 2-CH₃ 1 O O CH₃ 1372 D2 2-CH₃ H i-Pr 1 CH₃ H 2-CH₃ 1 O O CH₃1373 D2 2-CH₃ CH₃ Et 1 CH₃ H 2-CH₃ 1 O O CH₃ 1374 D2 2-CH₃ H F 1 CH₃ H2-CH₃ 1 O O CH₃ 1375 D2 2-CH₃ F F 1 CH₃ H 2-CH₃ 1 O O CH₃ 1376 D2 2-CH₃H CF₃ 1 CH₃ H 2-CH₃ 1 O O CH₃ 1377 D2 2-CH₃ H c-Pr 1 CH₃ H 2-CH₃ 1 O OCH₃ 1378 D2 2-CH₃ —CH2CH2— 1 CH₃ H 2-CH₃ 1 O O CH₃ 1379 D2 2-CH₃—CH2CH2CH2— 1 CH₃ H 2-CH₃ 1 O O CH₃ 1380 D2 2-CH₃ —CH2CH(CH3)— 1 CH₃ H2-CH₃ 1 O O CH₃ 1381 D2 2-CH₃ —CH2C(CH3)2— 1 CH₃ H 2-CH₃ 1 O O CH₃ 1382D2 2-CH₃ H H 1 H H 2-CH₃ 1 O O CH₃ 1383 D2 2-CH₃ H H 1 Et H 2-CH₃ 1 O OCH₃ 1384 D2 2-CH₃ H H 1 c-Pr H 2-CH₃ 1 O O CH₃ 1385 D2 2-CH₃ H H 1CH═CH₂ H 2-CH₃ 1 O O CH₃ 1386 D2 2-CH₃ H H 1 CH₂CH═CH₂ H 2-CH₃ 1 O O CH₃1387 D2 2-CH₃ H H 1 ethynyl H 2-CH₃ 1 O O CH₃ 1388 D2 2-CH₃ H H 1Propargyl H 2-CH₃ 1 O O CH₃ 1389 D2 2-CH₃ H H 1 CF₃ H 2-CH₃ 1 O O CH₃1390 D2 2-CH₃ H H 1 CH═CHCl H 2-CH₃ 1 O O CH₃ 1391 D2 2-CH₃ H H 13,3,2-tri-Iodo-allyl H 2-CH₃ 1 O O CH₃ 1392 D2 2-CH₃ H H 13-Iodopropargyl H 2-CH₃ 1 O O CH₃ 1393 D2 2-CH₃ H H 1 CN H 2-CH₃ 1 O OCH₃ 1394 D2 2-CF₃ H H 1 CN H 2-CH₃ 1 O O CH₃ 1395 D2 2-CH₃ H H 1 NO₂ H2-CH₃ 1 O O CH₃ 1396 D2 2-CH₃ H H 1 NH₂ H 2-CH₃ 1 O O CH₃ 1397 D2 2-CH₃H H 1 NHCH₃ H 2-CH₃ 1 O O CH₃ 1398 D2 2-CH₃ H H 1 N(CH₃)₂ H 2-CH₃ 1 O OCH₃ 1399 D2 2-CH₃ H H 1 CH₃ CH₃ 2-CH₃ 1 O O CH₃ 1400 D2 2-CH₃ H H 1 CH₃Et 2-CH₃ 1 O O CH₃

TABLE 24 1401 D2 2-CH₃ H H 1 CH₃ CH₃CO 2-CH₃ 1 O O CH₃ 1402 D2 2-CH₃ H H1 CH₃ CH₃CH₂CO 2-CH₃ 1 O O CH₃ 1403 D2 2-CH₃ H H 1 CH₃ PhCO 2-CH₃ 1 O OCH₃ 1404 D2 2-CH₃ H H 1 CH₃ 4-Cl-PhCO 2-CH₃ 1 O O CH₃ 1405 D2 2-CH₃ H H1 CH₃ PhCH₂CO 2-CH₃ 1 O O CH₃ 1406 D2 2-CH₃ H H 1 CH₃ CHO 2-CH₃ 1 O OCH₃ 1407 D2 2-CH₃ H H 1 CH₃ CH₃OCH₂ 2-CH₃ 1 O O CH₃ 1408 D2 2-CH₃ H H 1CH₃ CH₃CH(OCH₃) 2-CH₃ 1 O O CH₃ 1409 D2 2-CH₃ H H 1 CH₃ CH₃SO₂ 2-CH₃ 1 OO CH₃ 1410 D2 2-CH₃ H H 1 CH₃ PhSO₂ 2-CH₃ 1 O O CH₃ 1411 D2 2-CH₃ H H 1CH₃ 4-CH₃-PhSO₂ 2-CH₃ 1 O O CH₃ 1412 D2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 S OCH₃ 1413 D2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O S CH₃ 1414 D2 2-CH₃ H H 1 CH₃ H2-CH₃ 1 O — CH₃ 1415 D2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O NH CH₃ 1416 D2 2-CH₃H H 1 CH₃ H 2-CH₃ 1 O NCH₃ CH₃ 1417 D2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O H1418 D2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O Et 1419 D2 2-CH₃ H H 1 CH₃ H 2-CH₃1 O O n-Pr 1420 D2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CH═CH₂ 1421 D2 2-CH₃H H 1 CH₃ H 2-CH₃ 1 O O CH═CH₂ 1422 D2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O OPropargyl 1423 D2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O ethynyl 1424 D2 2-CH₃ HH 1 CH₃ H 2-CH₃ 1 O O CF₃ 1425 D2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CF₃1426 D2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CF₂CF₃ 1427 D2 2-CH₃ H H 1 CH₃ H2-CH₃ 1 O O CF₂CF₂H 1428 D2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CH═CHCl1429 D2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O 3-Iodo-propargyl 1430 D2 2-CH₃ H H1 CH₃ H 2-CH₃ 1 O O c-Pr 1431 D2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O c-Hex1432 D2 2-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O 2-CH₃-c-Pr 1433 E1 — H H 1 CH₃ H —0 O O CH₃ 1434 E1 — H H 1 CH₃ H 2-Cl 1 O O CH₃ 1435 E1 3-CH₃ H H 1 CH₃ H2-Cl 1 O O CH₃ 1436 E1 3-Et H H 1 CH₃ H 2-Cl 1 O O CH₃ 1437 E1 3-CF₃ H H1 CH₃ H 2-Cl 1 O O CH₃ 1438 E1 4-CF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1439 E13-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 1440 E1 3-Cl H H 1 CH₃ H 2-Cl 1 O O CH₃1441 E1 3-OCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1442 E1 3-OEt H H 1 CH3 H 2-Cl1 O O CH₃ 1443 E1 3-OCF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1444 E1 6-CH₃ H H 1CH₃ H 2-Cl 1 O O CH₃ 1445 E1 6-Et H H 1 CH₃ H 2-Cl 1 O O CH₃ 1446 E16-CF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1447 E1 6-F H H 1 CH₃ H 2-Cl 1 O O CH₃1448 E1 6-Cl H H 1 CH₃ H 2-Cl 1 O O CH₃ 1449 E1 6-OCH₃ H H 1 CH₃ H 2-Cl1 O O CH₃ 1450 E1 6-OEt H H 1 CH₃ H 2-Cl 1 O O CH₃ 1451 E1 6-OCF₃ H H 1CH₃ H 2-Cl 1 O O CH₃ 1452 E1 3,6-diCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1453E1 3-Et-6-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1454 E1 3-CF₃-6-F H H 1 CH₃ H2-Cl 1 O O CH₃ 1455 E1 3,6-diF H H 1 CH₃ H 2-Cl 1 O O CH₃ 1456 E13-Cl-6-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 1457 E1 3,6-diOCH₃ H H 1 CH₃ H 2-Cl1 O O CH₃ 1458 E1 3-OEt-6-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1459 E13-OCF₃-6-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 1460 E1 3-CH₃ H CH₃ 1 CH₃ H 2-Cl 1O O CH₃ 1461 E1 3-Et H CH₃ 1 CH₃ H 2-Cl 1 O O CH₃ 1462 E1 6-Et H CH₃ 1CH₃ H 2-Cl 1 O O CH₃

TABLE 25 1463 E1 6-Cl H CH₃ 1 CH₃ H 2-Cl 1 O O CH₃ 1464 E1 6-Cl H Et 1CH₃ H 2-Cl 1 O O CH₃ 1465 E1 6-Cl H i-Pr 1 CH₃ H 2-Cl 1 O O CH₃ 1466 E13-CH₃ H Et 1 CH₃ H 2-Cl 1 O O CH₃ 1467 E1 3-CH₃ H i-Pr 1 CH₃ H 2-Cl 1 OO CH₃ 1468 E1 3-CH₃ CH₃ Et 1 CH₃ H 2-Cl 1 O O CH₃ 1469 E1 3-CH₃ H F 1CH₃ H 2-Cl 1 O O CH₃ 1470 E1 3-CH₃ F F 1 CH₃ H 2-Cl 1 O O CH₃ 1471 E13-CH₃ H CF₃ 1 CH₃ H 2-Cl 1 O O CH₃ 1472 E1 3-CH₃ H c-Pr 1 CH₃ H 2-Cl 1 OO CH₃ 1473 E1 3-CH₃ —CH2CH2— 1 CH₃ H 2-Cl 1 O O CH₃ 1474 E1 3-CH₃—CH2CH2CH2— 1 CH₃ 1-1 2-Cl 1 O O CH₃ 1475 E1 3-CH₃ —CH2CH(CH3)— 1 CH₃ H2-Cl 1 O O CH₃ 1476 E1 3-CH₃ —CH2C(CH3)2— 1 CH₃ H 2-Cl 1 O O CH₃ 1477 E13-CH₃ H H 1 H H 2-Cl 1 O O CH₃ 1478 E1 3-CH₃ H H 1 Et H 2-Cl 1 O O CH₃1479 E1 3-CH₃ H H 1 c-Pr H 2-Cl 1 O O CH₃ 1480 E1 3-CH₃ H H 1 CH═CH₂ H2-Cl 1 O O CH₃ 1481 E1 3-CH₃ H H 1 CH₂CH═CH₂ H 2-Cl 1 O O CH₃ 1482 E13-CH₃ H H 1 ethynyl H 2-Cl 1 O O CH₃ 1483 E1 3-CH₃ H H 1 Propargyl H2-Cl 1 O O CH₃ 1484 E1 3-CH₃ H H 1 CF₃ H 2-Cl 1 O O CH₃ 1485 E1 3-CH₃ HH 1 CH═CHCl H 2-Cl 1 O O CH₃ 1486 E1 3-CH₃ H H 1 3,3,2-tri-Indo-allyl H2-Cl 1 O O CH₃ 1487 E1 3-CH₃ H H 1 3-Iodopropargyl H 2-Cl 1 O O CH₃ 1488E1 3-CH₃ H H 1 CN H 2-Cl 1 O O CH₃ 1489 E1 3-CF₃ H H 1 CN H 2-Cl 1 O OCH₃ 1490 E1 3-CH₃ H H 1 NO₂ H 2-Cl 1 O O CH₃ 1491 E1 3-CH₃ H H 1 NH₂ H2-Cl 1 O O CH₃ 1492 E1 3-CH₃ H H 1 NHCH₃ H 2-Cl 1 O O CH₃ 1493 E1 3-CH₃H H 1 N(CH₃)₂ H 2-Cl 1 O O CH₃ 1494 E1 3-CH₃ H H 1 CH₃ CH₃ 2-Cl 1 O OCH₃ 1495 E1 3-CH₃ H H 1 CH₃ Et 2-Cl 1 O O CH₃ 1496 E1 3-CH₃ H H 1 CH₃CH₃CO 2-Cl 1 O O CH₃ 1497 E1 3-CH₃ H H 1 CH₃ CH₃CH₂CO 2-Cl 1 O O CH₃1498 E1 3-CH₃ H H 1 CH₃ PhCO 2-Cl 1 O O CH₃ 1499 E1 3-CH₃ H H 1 CH₃4-Cl-PhCO 2-Cl 1 O O CH₃ 1500 E1 3-CH₃ H H 1 CH₃ PhCH₂CO 2-Cl 1 O O CH₃1501 E1 3-CH₃ H H 1 CH₃ CHO 2-Cl 1 O O CH₃ 1502 E1 3-CH₃ H H 1 CH₃CH₃OCH₂ 2-Cl 1 O O CH₃ 1503 E1 3-CH₃ H H 1 CH₃ CH₃CH(OCH₃) 2-Cl 1 O OCH₃ 1504 E1 3-CH₃ H H 1 CH₃ CH₃SO₂ 2-Cl 1 O O CH₃ 1505 E1 3-CH₃ H H 1CH₃ PhSO₂ 2-Cl 1 O O CH₃ 1506 E1 3-CH₃ H H 1 CH₃ 4-CH₃-PhSO₂ 2-Cl 1 O OCH₃ 1507 E1 3-CH₃ H H 1 CH₃ H 2-Cl 1 S O CH₃ 1508 E1 3-CH₃ H H 1 CH₃ H2-Cl 1 O S CH₃ 1509 E1 3-CH₃ H H 1 CH₃ H 2-Cl 1 O — CH₃ 1510 E1 3-CH₃ HH 1 CH₃ H 2-Cl 1 O NH CH₃ 1511 E1 3-CH₃ H H 1 CH₃ H 2-Cl 1 O NCH₃ CH₃1512 E1 3-CH₃ H H 1 CH₃ H 2-Cl 1 O O H 1513 E1 3-CH₃ H H 1 CH₃ H 2-Cl 1O O Et 1514 E1 3-CH₃ H H 1 CH₃ H 2-Cl 1 O O n-Pr 1515 E1 3-CH₃ H H 1 CH₃H 2-Cl 1 O O CH₂CH═CH₂ 1516 E1 3-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH═CH₂ 1517E1 3-CH₃ H H 1 CH₃ H 2-Cl 1 O O Propargyl 1518 E1 3-CH₃ H H 1 CH₃ H 2-Cl1 O O ethynyl 1519 E1 3-CH₃ H H 1 CH₃ H 2-Cl 1 O O CF₃ 1520 E1 3-CH₃ H H1 CH₃ H 2-Cl 1 O O CH₂CF₃ 1521 E1 3-CH₃ H H 1 CH₃ H 2-Cl 1 O O CF₂CF₃1522 E1 3-CH₃ H H 1 CH₃ H 2-Cl 1 O O CF₂CF₂H 1523 E1 3-CH₃ H H 1 CH₃ H2-Cl 1 O O CH₂CH═CHCl 1524 E1 3-CH₃ H H 1 CH₃ H 2-Cl 1 O O3-Iodo-propargyl

TABLE 26 1525 E1 3-CH₃ H H 1 CH₃ H 2-Cl 1 O O c-Pr 1526 E1 3-CH₃ H H 1CH₃ H 2-Cl 1 O O c-Hex 1527 E1 3-CH₃ H H 1 CH₃ H 2-Cl 1 O O 2-CH₃-c-Pr1528 E1 — H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1529 E1 3-CH₃ H H 1 CH₃ H 2-CH₃ 1O O CH₃ 1530 E1 3-Et H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1531 E1 3-CF₃ H H 1 CH₃H 2-CH₃ 1 O O CH₃ 1532 E1 3-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1533 E1 3-Cl HH 1 CH₃ H 2-CH₃ 1 O O CH₃ 1534 E1 3-OCH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃1535 E1 3-OEt H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1536 E1 3-OCF₃ H H 1 CH₃ H2-CH₃ 1 O O CH₃ 1537 E1 6-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1538 E1 6-Et HH 1 CH₃ H 2-CH₃ 1 O O CH₃ 1539 E1 6-CF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1540E1 6-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1541 E1 6-Cl H H 1 CH₃ H 2-CH₃ 1 O OCH₃ 1542 E1 6-OCH₃ H H 1 CH₃ 11 2-CH₃ 1 O O CH₃ 1543 E1 6-OEt H H 1 CH₃H 2-CH₃ 1 O O CH₃ 1544 E1 6-OCF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1545 E13,6-diCH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1546 E1 3-Et-6-CH₃ H H 1 CH₃ H2-CH₃ 1 O O CH₃ 1547 E1 3-CF₃-6-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1548 E13,6-diF H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1549 E1 3-Cl-6-F H H 1 CH₃ H 2-CH₃ 1O O CH₃ 1550 E1 3,6-diOCH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1551 E13-OEt-6-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1552 E1 3-OCF₃-6-F H H 1 CH₃ H2-CH₃ 1 O O CH₃ 1553 E1 3-CH₃ H CH₃ 1 CH₃ H 2-CH₃ 1 O O CH₃ 1554 E1 3-EtH CH₃ 1 CH₃ H 2-CH₃ 1 O O CH₃ 1555 E1 6-Et H CH₃ 1 CH₃ H 2-CH₃ 1 O O CH₃1556 E1 3-CH₃ H Et 1 CH₃ H 2-CH₃ 1 O O CH₃ 1557 E1 3-CH₃ H i-Pr 1 CH₃ H2-CH₃ 1 O O CH₃ 1558 E1 3-CH₃ CH₃ Et 1 CH₃ H 2-CH₃ 1 O O CH₃ 1559 E13-CH₃ H F 1 CH₃ H 2-CH₃ 1 O O CH₃ 1560 E1 3-CH₃ F F 1 CH₃ H 2-CH₃ 1 O OCH₃ 1561 E1 3-CH₃ H CF₃ 1 CH₃ H 2-CH₃ 1 O O CH₃ 1562 E1 3-CH₃ H c-Pr 1CH₃ H 2-CH₃ 1 O O CH₃ 1563 E1 3-CH₃ —CH2CH2— 1 CH₃ H 2-CH₃ 1 O O CH₃1564 E1 3-CH₃ —CH2CH2OH2— 1 CH₃ H 2-CH₃ 1 O O CH₃ 1565 E1 3-CH₃—CH2CH(CH3)— 1 CH₃ H 2-CH₃ 1 O O CH₃ 1566 E1 3-CH₃ —CH2C(CH3)2— 1 CH₃ H2-CH₃ 1 O O CH₃ 1567 E1 3-CH₃ H H 1 H H 2-CH₃ 1 O O CH₃ 1568 E1 3-CH₃ HH 1 Et H 2-CH₃ 1 O O CH₃ 1569 E1 3-CH₃ H H 1 c-Pr H 2-CH₃ 1 O O CH₃ 1570E1 3-CH₃ H H 1 CH═CH₂ H 2-CH₃ 1 O O CH₃ 1571 E1 3-CH₃ H H 1 CH₂CH═CH₂ H2-CH₃ 1 O O CH₃ 1572 E1 3-CH₃ H H 1 ethynyl H 2-CH₃ 1 O O CH₃ 1573 E13-CH₃ H H 1 Propargyl H 2-CH₃ 1 O O CH₃ 1574 E1 3-CH₃ H H 1 CF₃ H 2-CH₃1 O O CH₃ 1575 E1 3-CH₃ H H 1 CH═CHCl H 2-CH₃ 1 O O CH₃ 1576 E1 3-CH₃ HH 1 3,3,2-tri-Iodo-allyl H 2-CH₃ 1 O O CH₃ 1577 E1 3-CH₃ H H 13-Iodopropargyl H 2-CH₃ 1 O O CH₃ 1578 E1 3-CH₃ H H 1 CN H 2-CH₃ 1 O OCH₃ 1579 E1 3-CH₃ H H 1 CN H 2-CH₃ 1 O O CH₃ 1580 E1 3-CH₃ H H 1 NO₂ H2-CH₃ 1 O O CH₃ 1581 E1 3-CH₃ H H 1 NH₂ H 2-CH₃ 1 O O CH₃ 1582 E1 3-CH₃H H 1 NHCH₃ H 2-CH₃ 1 O O CH₃ 1583 E1 3-CH₃ H H 1 N(CH₃)₂ H 2-CH₃ 1 O OCH₃ 1584 E1 3-CH₃ H H 1 CH₃ CH₃ 2-CH₃ 1 O O CH₃ 1585 E1 3-CH₃ H H 1 CH₃Et 2-CH₃ 1 O O CH₃ 1586 E1 3-CH₃ H H 1 CH₃ CH₃CO 2-CH₃ 1 O O CH₃

TABLE 27 1587 E1 3-CH₃ H H 1 CH₃ CH₃CH₂CO 2-CH₃ 1 O O CH₃ 1588 E1 3-CH₃H H 1 CH₃ PhCO 2-CH₃ 1 O O CH₃ 1589 E1 3-CH₃ H H 1 CH₃ 4-Cl-PhCO 2-CH₃ 1O O CH₃ 1590 E1 3-CH₃ H H 1 CH₃ PhCH₂CO 2-CH₃ 1 O O CH₃ 1591 E1 3-CH₃ HH 1 CH₃ CHO 2-CH₃ 1 O O CH₃ 1592 E1 3-CH₃ H H 1 CH₃ CH₃OCH₂ 2-CH₃ 1 O OCH₃ 1593 E1 3-CH₃ H H 1 CH₃ CH₃CH(OCH₃) 2-CH₃ 1 O O CH₃ 1594 E1 3-CH₃ HH 1 CH₃ CH₃SO₂ 2-CH₃ 1 O O CH₃ 1595 E1 3-CH₃ H H 1 CH₃ PhSO₂ 2-CH₃ 1 O OCH₃ 1596 E1 3-CH₃ H H 1 CH₃ 4-CH₃-PhSO₂ 2-CH₃ 1 O O CH₃ 1597 E1 3-CH₃ HH 1 CH₃ H 2-CH₃ 1 S O CH₃ 1598 E1 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 O S CH₃ 1599E1 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 O — CH₃ 1600 E1 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 ONH CH₃ 1601 E1 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 O NCH₃ CH₃ 1602 E1 3-CH₃ H H 1CH₃ H 2-CH₃ 1 O O H 1603 E1 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O Et 1604 E13-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O n-Pr 1605 E1 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 O OCH₂CH═CH₂ 1606 E1 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH═CH₂ 1607 E1 3-CH₃ H H1 CH₃ H 2-CH₃ 1 O O Propargyl 1608 E1 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 O Oethynyl 1609 E1 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CF₃ 1610 E1 3-CH₃ H H 1CH₃ H 2-CH₃ 1 O O CH₂CF₃ 1611 E1 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CF₂CF₃1612 E1 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CF₂CF₂H 1613 E1 3-CH₃ H H 1 CH₃ H2-CH₃ 1 O O CH₂CH═CHCl 1614 E1 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O3-Iodo-propargyl 1615 E1 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O c-Pr 1616 E13-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O c-Hex 1617 E1 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 OO 2-CH₃-c-Pr 1618 E2 — H H 1 CH₃ H — 0 O O CH₃ 1619 E2 — H H 1 CH₃ H2-Cl 1 O O CH₃ 1620 E2 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1621 E2 4-Et H H1 CH₃ H 2-Cl 1 O O CH₃ 1622 E2 4-CF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1623 E24-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 1624 E2 4-Cl H H 1 CH₃ H 2-Cl 1 O O CH₃1625 E2 4-OCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1626 E2 4-OEt H H 1 CH₃ H 2-Cl1 O O CH₃ 1627 E2 4-OCF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1628 E2 6-CH₃ H H 1CH₃ H 2-Cl 1 O O CH₃ 1629 E2 6-Et H H 1 CH₃ H 2-Cl 1 O O CH₃ 1630 E26-CF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1631 E2 6-F H H 1 CH₃ H 2-Cl 1 O O CH₃1632 E2 6-Cl H H 1 CH₃ H 2-Cl 1 O O CH₃ 1633 E2 6-OCH₃ H H 1 CH₃ H 2-Cl1 O O CH₃ 1634 E2 6-OEt H H 1 CH₃ H 2-Cl 1 O O CH₃ 1635 E2 6-OCF₃ H H 1CH₃ H 2-Cl 1 O O CH₃ 1636 E2 4,6-diCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1637E2 4-Et-6-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1638 E2 4-CF₃-6-F 14 H 1 CH₃ H2-Cl 1 O O CH₃ 1639 E2 4,6-diF H H 1 CH₃ H 2-Cl 1 O O CH₃ 1640 E24-Cl-6-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 1641 E2 4,6-diOCH₃ H H 1 CH₃ H 2-Cl1 O O CH₃ 1642 E2 4-OEt-6-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1643 E24-OCF₃-6-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 1644 E2 4-CH₃ H CH₃ 1 CH₃ H 2-Cl 1O O CH₃ 1645 E2 4-Et H CH₃ 1 CH₃ H 2-Cl 1 O O CH₃ 1646 E2 6-Et H CH₃ 1CH₃ H 2-Cl 1 O O CH₃ 1647 E2 6-Cl H CH₃ 1 CH₃ H 2-Cl 1 O O CH₃ 1648 E26-Cl H Et 1 CH₃ H 2-Cl 1 O O CH₃

TABLE 28 1649 E2 6-Cl H i-Pr 1 CH₃ H 2-Cl 1 O O CH₃ 1650 E2 4-CH₃ H Et 1CH₃ H 2-Cl 1 O O CH₃ 1651 E2 4-CH₃ H i-Pr 1 CH₃ H 2-Cl 1 O O CH₃ 1652 E24-CH₃ CH₃ Et 1 CH₃ H 2-Cl 1 O O CH₃ 1653 E2 4-CH₃ H F 1 CH₃ H 2-Cl 1 O OCH₃ 1654 E2 4-CH₃ F F 1 CH₃ H 2-Cl 1 O O CH₃ 1655 E2 4-CH₃ H CF₃ 1 CH₃ H2-Cl 1 O O CH₃ 1656 E2 4-CH₃ H c-Pr 1 CH₃ H 2-Cl 1 O O CH₃ 1657 E2 4-CH₃—CH2CH2— 1 CH₃ H 2-Cl 1 O O CH₃ 1658 E2 4-CH₃ —CH2CH2CH2— 1 CH₃ H 2-Cl 1O O CH₃ 1659 E2 4-CH₃ —CH2CH(CH3)— 1 CH₃ H 2-Cl 1 O O CH₃ 1660 E2 4-CH₃—CH2C(CH3)2— 1 CH₃ H 2-Cl 1 O O CH₃ 1661 E2 4-CH₃ H H 1 H H 2-Cl 1 O OCH₃ 1662 E2 4-CH₃ H H 1 Et H 2-Cl 1 O O CH₃ 1663 E2 4-CH₃ H H 1 c-Pr H2-Cl 1 O O CH₃ 1664 E2 4-CH₃ H H 1 CH═CH₂ H 2-Cl 1 O O CH₃ 1665 E2 4-CH₃H H 1 CH₂CH═CH₂ H 2-Cl 1 O O CH₃ 1666 E2 4-CH₃ H H 1 ethynyl H 2-Cl 1 OO CH₃ 1667 E2 4-CH₃ H H 1 Propargyl H 2-Cl 1 O O CH₃ 1668 E2 4-CH₃ H H 1CF₃ H 2-Cl 1 O O CH₃ 1669 E2 4-CH₃ H H 1 CH═CHCl H 2-Cl 1 O O CH₃ 1670E2 4-CH₃ H H 1 3,3,2-tri-Iodo-allyl H 2-Cl 1 O O CH₃ 1671 E2 4-CH₃ H H 13-Iodopropargyl H 2-Cl 1 O O CH₃ 1672 E2 4-CH₃ H H 1 CN H 2-Cl 1 O O CH₃1673 E2 4-CF₃ H H 1 CN H 2-Cl 1 O O CH₃ 1674 E2 4-CH₃ H H 1 NO₂ H 2-Cl 1O O CH₃ 1675 E2 4-CH₃ H H 1 NH₂ H 2-Cl 1 O O CH₃ 1676 E2 4-CH₃ H H 1NHCH₃ H 2-Cl 1 O O CH₃ 1677 E2 4-CH₃ H H 1 N(CH₃)₂ H 2-Cl 1 O O CH₃ 1678E2 4-CH₃ H H 1 CH₃ CH₃ 2-Cl 1 O O CH₃ 1679 E2 4-CH₃ H H 1 CH₃ Et 2-Cl 1O O CH₃ 1680 E2 4-CH₃ H H 1 CH₃ CH₃CO 2-Cl 1 O O CH₃ 1681 E2 4-CH₃ H H 1CH₃ CH₃CH₂CO 2-Cl 1 O O CH₃ 1682 E2 4-CH₃ H H 1 CH₃ PhCO 2-Cl 1 O O CH₃1683 E2 4-CH₃ H H 1 CH₃ 4-Cl-PhCO 2-Cl 1 O O CH₃ 1684 E2 4-CH₃ H H 1 CH₃PhCH₂CO 2-Cl 1 O O CH₃ 1685 E2 4-CH₃ H H 1 CH₃ CHO 2-Cl 1 O O CH₃ 1686E2 4-CH₃ H H 1 CH₃ CH₃OCH₂ 2-Cl 1 O O CH₃ 1687 E2 4-CH₃ H H 1 CH₃CH₃CH(OCH₃) 2-Cl 1 O O CH₃ 1688 E2 4-CH₃ H H 1 CH₃ CH₃SO₂ 2-Cl 1 O O CH₃1689 E2 4-CH₃ H H 1 CH₃ PhSO₂ 2-Cl 1 O O CH₃ 1690 E2 4-CH₃ H H 1 CH₃4-CH₃-PhSO₂ 2-Cl 1 O O CH₃ 1691 E2 4-CH₃ H H 1 CH₃ H 2-Cl 1 S O CH₃ 1692E2 4-CH₃ H H 1 CH₃ H 2-Cl 1 O S CH₃ 1693 E2 4-CH₃ H H 1 CH₃ H 2-Cl 1 O —CH₃ 1694 E2 4-CH₃ H H 1 CH₃ H 2-Cl 1 O NH CH₃ 1695 E2 4-CH₃ H H 1 CH₃ H2-Cl 1 O NCH₃ CH₃ 1696 E2 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O H 1697 E2 4-CH₃ HH 1 CH₃ H 2-Cl 1 O O Et 1698 E2 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O n-Pr 1699E2 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₂CH═CH₂ 1700 E2 4-CH₃ H H 1 CH₃ H 2-Cl1 O O CH═CH₂ 1701 E2 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O Propargyl 1702 E24-CH₃ H H 1 CH₃ H 2-Cl 1 O O ethynyl 1703 E2 4-CH₃ H H 1 CH₃ H 2-Cl 1 OO CF₃ 1704 E2 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₂CF₃ 1705 E2 4-CH₃ H H 1CH₃ H 2-Cl 1 O O CF₂CF₃ 1706 E2 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O CF₂CF₂H1707 E2 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₂CH═CHCl 1708 E2 4-CH₃ H H 1 CH₃H 2-Cl 1 O O 3-Iodo-propargyl 1709 E2 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O c-Pr1710 E2 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O c-Hex

TABLE 29 1711 E2 4-CH₃ H H 1 CH₃ H 2-Cl 1 O O 2-CH₃-c-Pr 1712 E2 — H H 1CH₃ H 2-CH₃ 1 O O CH₃ 1713 E2 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1714 E24-Et H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1715 E2 4-CF₃ H H 1 CH₃ H 2-CH₃ 1 O OCH₃ 1716 E2 4-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1717 E2 4-Cl H H 1 CH₃ H2-CH₃ 1 O O CH₃ 1718 E2 4-OCH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1719 E2 4-OEtH H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1720 E2 4-OCF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃1721 E2 6-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1722 E2 6-Et H H 1 CH₃ H 2-CH₃1 O O CH₃ 1723 E2 6-CF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1724 E2 6-F H H 1CH₃ H 2-CH₃ 1 O O CH₃ 1725 E2 6-Cl H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1726 E26-OCH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1727 E2 6-OEt H H 1 CH₃ H 2-CH₃ 1 O OCH₃ 1728 E2 6-OCF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1729 E2 4,6-diCH₃ H H 1CH₃ H 2-CH₃ 1 O O CH₃ 1730 E2 4-Et-6-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃1731 E2 4-CF₃-6-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1732 E2 4,6-diF H H 1 CH₃H 2-CH₃ 1 O O CH₃ 1733 E2 4-Cl-6-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1734 E24,6-diOCH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1735 E2 4-OEt-6-CH₃ H H 1 CH₃ H2-CH₃ 1 O O CH₃ 1736 E2 4-OCF₃-6-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1737 E24-CH₃ H CH₃ 1 CH₃ H 2-CH₃ 1 O O CH₃ 1738 E2 4-Et H CH₃ 1 CH₃ H 2-CH₃ 1 OO CH₃ 1739 E2 6-Et H CH₃ 1 CH₃ H 2-CH₃ 1 O O CH₃ 1740 E2 4-CH₃ H Et 1CH₃ H 2-CH₃ 1 O O CH₃ 1741 E2 4-CH₃ H i-Pr 1 CH₃ H 2-CH₃ 1 O O CH₃ 1742E2 4-CH₃ CH₃ Et 1 CH₃ H 2-CH₃ 1 O O CH₃ 1743 E2 4-CH₃ H F 1 CH₃ H 2-CH₃1 O O CH₃ 1744 E2 4-CH₃ F F 1 CH₃ H 2-CH₃ 1 O O CH₃ 1745 E2 4-CH₃ H CF₃1 CH₃ H 2-CH₃ 1 O O CH₃ 1746 E2 4-CH₃ H c-Pr 1 CH₃ H 2-CH₃ 1 O O CH₃1747 E2 4-CH₃ —CH2CH2— 1 CH₃ H 2-CH₃ 1 O O CH₃ 1748 E2 4-CH₃ —CH2CH2CH2—1 CH₃ H 2-CH₃ 1 O O CH₃ 1749 E2 4-CH₃ —CH2CH(CH3)— 1 CH₃ H 2-CH₃ 1 O OCH₃ 1750 E2 4-CH₃ —CH2C(CH3)2— 1 CH₃ H 2-CH₃ 1 O O CH₃ 1751 E2 4-CH₃ H H1 H H 2-CH₃ 1 O O CH₃ 1752 E2 4-CH₃ H H 1 Et H 2-CH₃ 1 O O CH₃ 1753 E24-CH₃ H H 1 c-Pr H 2-CH₃ 1 O O CH₃ 1754 E2 4-CH₃ H H 1 CH═CH₂ H 2-CH₃ 1O O CH₃ 1755 E2 4-CH₃ H H 1 CH₂CH═CH₂ H 2-CH₃ 1 O O CH₃ 1756 E2 4-CH₃ HH 1 ethynyl H 2-CH₃ 1 O O CH₃ 1757 E2 4-CH₃ H H 1 Propargyl H 2-CH₃ 1 OO CH₃ 1758 E2 4-CH₃ H H 1 CF₃ H 2-CH₃ 1 O O CH₃ 1759 E2 4-CH₃ H H 1CH═CHCl H 2-CH₃ 1 O O CH₃ 1760 E2 4-CH₃ H H 1 3,3,2-tri-Iodo-allyl H2-CH₃ 1 O O CH₃ 1761 E2 4-CH₃ H H 1 3-Iodopropargyl H 2-CH₃ 1 O O CH₃1762 E2 4-CH₃ H H 1 CN H 2-CH₃ 1 O O CH₃ 1763 E2 4-CH₃ H H 1 CN H 2-CH₃1 O O CH₃ 1764 E2 4-CH₃ H H 1 NO₂ H 2-CH₃ 1 O O CH₃ 1765 E2 4-CH₃ H H 1NH₂ H 2-CH₃ 1 O O CH₃ 1766 E2 4-CH₃ H H 1 NHCH₃ H 2-CH₃ 1 O O CH₃ 1767E2 4-CH₃ H H 1 N(CH₃)₂ H 2-CH₃ 1 O O CH₃ 1768 E2 4-CH₃ H H 1 CH₃ CH₃2-CH₃ 1 O O CH₃ 1769 E2 4-CH₃ H H 1 CH₃ Et 2-CH₃ 1 O O CH₃ 1770 E2 4-CH₃H H 1 CH₃ CH₃CO 2-CH₃ 1 O O CH₃ 1771 E2 4-CH₃ H H 1 CH₃ CH₃CH₂CO 2-CH₃ 1O O CH₃ 1772 E2 4-CH₃ H H 1 CH₃ PhCO 2-CH₃ 1 O O CH₃

TABLE 30 1773 E2 4-CH₃ H H 1 CH₃ 4-Cl-PhCO 2-CH₃ 1 O O CH₃ 1774 E2 4-CH₃H H 1 CH₃ PhCH₂CO 2-CH₃ 1 O O CH₃ 1775 E2 4-CH₃ H H 1 CH₃ CHO 2-CH₃ 1 OO CH₃ 1776 E2 4-CH₃ H H 1 CH₃ CH₃OCH₂ 2-CH₃ 1 O O CH₃ 1777 E2 4-CH₃ H H1 CH₃ CH₃CH(OCH₃) 2-CH₃ 1 O O CH₃ 1778 E2 4-CH₃ H H 1 CH₃ CH₃SO₂ 2-CH₃ 1O O CH₃ 1779 E2 4-CH₃ H H 1 CH₃ PhSO₂ 2-CH₃ 1 O O CH₃ 1780 E2 4-CH₃ H H1 CH₃ 4-CH₃-PhSO₂ 2-CH₃ 1 O O CH₃ 1781 E2 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 S OCH₃ 1782 E2 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O S CH₃ 1783 E2 4-CH₃ H H 1 CH₃ H2-CH₃ 1 O — CH₃ 1784 E2 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O NH CH₃ 1785 E2 4-CH₃H H 1 CH₃ H 2-CH₃ 1 O NCH₃ CH₃ 1786 E2 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O H1787 E2 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O Et 1788 E2 4-CH₃ H H 1 CH₃ H 2-CH₃1 O O n-Pr 1789 E2 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CH═CH₂ 1790 E2 4-CH₃H H 1 CH₃ H 2-CH₃ 1 O O CH═CH₂ 1791 E2 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O OPropargyl 1792 E2 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O ethynyl 1793 E2 4-CH₃ HH 1 CH₃ H 2-CH₃ 1 O O CF₃ 1794 E2 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CF₃1795 E2 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CF₂CF₃ 1796 E2 4-CH₃ H H 1 CH₃ H2-CH₃ 1 O O CF₂CF₂H 1797 E2 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CH═CHCl1798 E2 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O 3-Iodo-propargyl 1799 E2 4-CH₃ H H1 CH₃ H 2-CH₃ 1 O O c-Pr 1800 E2 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O c-Hex1801 E2 4-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O 2-CH₃-c-Pr 1802 E3 — H H 1 CH₃ H —0 O O CH₃ 1803 E3 — H H 1 CH₃ H 2-Cl 1 O O CH₃ 1804 E3 3-CH₃ H H 1 CH₃ H2-Cl 1 O O CH₃ 1805 E3 3-Et H H 1 CH₃ H 2-Cl 1 O O CH₃ 1806 E3 3-CF₃ H H1 CH₃ H 2-Cl 1 O O CH₃ 1807 E3 3-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 1808 E33-Cl H H 1 CH₃ H 2-Cl 1 O O CH₃ 1809 E3 3-OCH₃ H H 1 CH₃ H 2-Cl 1 O OCH₃ 1810 E3 3-OEt H H 1 CH₃ H 2-Cl 1 O O CH₃ 1811 E3 3-OCF₃ H H 1 CH₃ H2-Cl 1 O O CH₃ 1812 E3 6-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1813 E3 6-Et H H1 CH₃ H 2-Cl 1 O O CH₃ 1814 E3 6-CF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1815 E36-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 1816 E3 6-Cl H H 1 CH₃ H 2-Cl 1 O O CH₃1817 E3 6-OCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1818 E3 6-OEt H H 1 CH₃ H 2-Cl1 O O CH₃ 1819 E3 6-OCF₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1820 E3 3,6-diCH₃ HH 1 CH₃ H 2-Cl 1 O O CH₃ 1821 E3 3-Et-6-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃1822 E3 3-CF₃-6-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 1823 E3 3,6-diF H H 1 CH₃ H2-Cl 1 O O CH₃ 1824 E3 3-Cl-6-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 1825 E33,6-diOCH₃ H H 1 CH₃ H 2-Cl 1 O O CH₃ 1826 E3 3-OEt-6-CH₃ H H 1 CH₃ H2-Cl 1 O O CH₃ 1827 E3 3-OCF₃-6-F H H 1 CH₃ H 2-Cl 1 O O CH₃ 1828 E33-CH₃ H CH₃ 1 CH₃ H 2-Cl 1 O O CH₃ 1829 E3 3-Et H CH₃ 1 CH₃ H 2-Cl 1 O OCH₃ 1830 E3 6-Et H CH₃ 1 CH₃ H 2-Cl 1 O O CH₃ 1831 E3 6-Cl H CH₃ 1 CH₃ H2-Cl 1 O O CH₃ 1832 E3 6-Cl H Et 1 CH₃ H 2-Cl 1 O O CH₃ 1833 E3 6-Cl Hi-Pr 1 CH₃ H 2-Cl 1 O O CH₃ 1834 E3 3-CH₃ H Et 1 CH₃ H 2-Cl 1 O O CH₃

TABLE 31 1835 E3 3-CH₃ H i-Pr 1 CH₃ H 2-Cl 1 O O CH₃ 1836 E3 3-CH₃ CH₃Et 1 CH₃ H 2-Cl 1 O O CH₃ 1837 E3 3-CH₃ H F 1 CH₃ H 2-Cl 1 O O CH₃ 1838E3 3-CH₃ F F 1 CH₃ H 2-Cl 1 O O CH₃ 1839 E3 3-CH₃ H CF₃ 1 CH₃ H 2-Cl 1 OO CH₃ 1840 E3 3-CH₃ H c-Pr 1 CH₃ H 2-Cl 1 O O CH₃ 1841 E3 3-CH₃ —CH2CH2—1 CH₃ H 2-Cl 1 O O CH₃ 1842 E3 3-CH₃ —CH2CH2CH2— 1 CH₃ H 2-Cl 1 O O CH₃1843 E3 3-CH₃ —CH2CH(CH3)— 1 CH₃ H 2-Cl 1 O O CH₃ 1844 E3 3-CH₃—CH2C(CH3)2— 1 CH₃ H 2-Cl 1 O O CH₃ 1845 E3 3-CH₃ H H 1 H H 2-Cl 1 O OCH₃ 1846 E3 3-CH₃ H H 1 Et H 2-Cl 1 O O CH₃ 1847 E3 3-CH₃ H H 1 c-Pr H2-Cl 1 O O CH₃ 1848 E3 3-CH₃ H H 1 CH═CH₂ H 2-Cl 1 O O CH₃ 1849 E3 3-CH₃H H 1 CH₂CH═CH₂ H 2-Cl 1 O O CH₃ 1850 E3 3-CH₃ H H 1 ethynyl H 2-Cl 1 OO CH₃ 1851 E3 3-CH₃ H H 1 Propargyl H 2-Cl 1 O O CH₃ 1852 E3 3-CH₃ H H 1CF₃ H 2-Cl 1 O O CH₃ 1853 E3 3-CH₃ H H 1 CH═CHCl H 2-Cl 1 O O CH₃ 1854E3 3-CH₃ H H 1 3,3,2-tri-Iodo-allyl H 2-Cl 1 O O CH₃ 1855 E3 3-CH₃ H H 13-Iodopropargyl H 2-Cl 1 O O CH₃ 1856 E3 3-CH₃ H H 1 CN H 2-Cl 1 O O CH₃1857 E3 3-CF₃ H H 1 CN H 2-Cl 1 O O CH₃ 1858 E3 3-CH₃ H H 1 NO₂ H 2-Cl 1O O CH₃ 1859 E3 3-CH₃ H H 1 NH₂ H 2-Cl 1 O O CH₃ 1860 E3 3-CH₃ H H 1NHCH₃ H 2-Cl 1 O O CH₃ 1861 E3 3-CH₃ H H 1 N(CH₃)₂ H 2-Cl 1 O O CH₃ 1862E3 3-CH₃ H H 1 CH₃ CH₃ 2-Cl 1 O O CH₃ 1863 E3 3-CH₃ H H 1 CH₃ Et 2-Cl 1O O CH₃ 1864 E3 3-CH₃ H H 1 CH₃ CH₃CO 2-Cl 1 O O CH₃ 1865 E3 3-CH₃ H H 1CH₃ CH₃CH₂CO 2-Cl 1 O O CH₃ 1866 E3 3-CH₃ H H 1 CH₃ PhCO 2-Cl 1 O O CH₃1867 E3 3-CH₃ H H 1 CH₃ 4-Cl-PhCO 2-Cl 1 O O CH₃ 1868 E3 3-CH₃ H H 1 CH₃PhCH₂CO 2-Cl 1 O O CH₃ 1869 E3 3-CH₃ H H 1 CH₃ CHO 2-Cl 1 O O CH₃ 1870E3 3-CH₃ H H 1 CH₃ CH₃OCH₂ 2-Cl 1 O O CH₃ 1871 E3 3-CH₃ H H 1 CH₃CH₃CH(OCH₃) 2-Cl 1 O O CH₃ 1872 E3 3-CH₃ H H 1 CH₃ CH₃SO₂ 2-Cl 1 O O CH₃1873 E3 3-CH₃ H H 1 CH₃ PhSO₂ 2-Cl 1 O O CH₃ 1874 E3 3-CH₃ H H 1 CH₃4-CH₃-PhSO₂ 2-Cl 1 O O CH₃ 1875 E3 3-CH₃ H H 1 CH₃ H 2-Cl 1 S O CH₃ 1876E3 3-CH₃ H H 1 CH₃ H 2-Cl 1 O S CH₃ 1877 E3 3-CH₃ H H 1 CH₃ H 2-Cl 1 O —CH₃ 1878 E3 3-CH₃ H H 1 CH₃ H 2-Cl 1 O NH CH₃ 1879 E3 3-CH₃ H H 1 CH₃ H2-Cl 1 O NCH₃ CH₃ 1880 E3 3-CH₃ H H 1 CH₃ H 2-Cl 1 O O H 1881 E3 3-CH₃ HH 1 CH₃ H 2-Cl 1 O O Et 1882 E3 3-CH₃ H H 1 CH₃ H 2-Cl 1 O O n-Pr 1883E3 3-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₂CH═CH₂ 1884 E3 3-CH₃ H H 1 CH₃ H 2-Cl1 O O CH═CH₂ 1885 E3 3-CH₃ H H 1 CH₃ H 2-Cl 1 O O Propargyl 1886 E33-CH₃ H H 1 CH₃ H 2-Cl 1 O O ethynyl 1887 E3 3-CH₃ H H 1 CH₃ H 2-Cl 1 OO CF₃ 1888 E3 3-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₂CF₃ 1889 E3 3-CH₃ H H 1CH₃ H 2-Cl 1 O O CF₂CF₃ 1890 E3 3-CH₃ H H 1 CH₃ H 2-Cl 1 O O CF₂CF₂H1891 E3 3-CH₃ H H 1 CH₃ H 2-Cl 1 O O CH₂CH═CHCl 1892 E3 3-CH₃ H H 1 CH₃H 2-Cl 1 O O 3-Iodo-propargyl 1893 E3 3-CH₃ H H 1 CH₃ H 2-Cl 1 O O c-Pr1894 E3 3-CH₃ H H 1 CH₃ H 2-Cl 1 O O c-Hex 1895 E3 3-CH₃ H H 1 CH₃ H2-Cl 1 O O 2-CH₃-c-Pr 1896 E3 — H H 1 CH₃ H 2-CH₃ 1 O O CH₃

TABLE 32 1897 E3 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1898 E3 3-Et H H 1CH₃ H 2-CH₃ 1 O O CH₃ 1899 E3 3-CF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1900 E33-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1901 E3 3-Cl H H 1 CH₃ H 2-CH₃ 1 O O CH₃1902 E3 3-OCH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1903 E3 3-OEt H H 1 CH₃ H2-CH₃ 1 O O CH₃ 1904 E3 3-OCF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1905 E3 6-CH₃H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1906 E3 6-Et H H 1 CH₃ H 2-CH₃ 1 O O CH₃1907 E3 6-CF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1908 E3 6-F H H 1 CH₃ H 2-CH₃1 O O CH₃ 1909 E3 6-Cl H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1910 E3 6-OCH₃ H H 1CH₃ H 2-CH₃ 1 O O CH₃ 1911 E3 6-OEt H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1912 E36-OCF₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1913 E3 3,6-diCH₃ H H 1 CH₃ H 2-CH₃ 1O O CH₃ 1914 E3 3-Et-6-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1915 E3 3-CF₃-6-FH H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1916 E3 3,6-diF H H 1 CH₃ H 2-CH₃ 1 O O CH₃1917 E3 3-Cl-6-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1918 E3 3,6-diOCH₃ H H 1CH₃ H 2-CH₃ 1 O O CH₃ 1919 E3 3-OEt-6-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₃1920 E3 3-OCF₃-6-F H H 1 CH₃ H 2-CH₃ 1 O O CH₃ 1921 E3 3-CH₃ H CH₃ 1 CH₃H 2-CH₃ 1 O O CH₃ 1922 E3 3-Et H CH₃ 1 CH₃ H 2-CH₃ 1 O O CH₃ 1923 E36-Et H CH₃ 1 CH₃ H 2-CH₃ 1 O O CH₃ 1924 E3 3-CH₃ H Et 1 CH₃ H 2-CH₃ 1 OO CH₃ 1925 E3 3-CH₃ H i-Pr 1 CH₃ H 2-CH₃ 1 O O CH₃ 1926 E3 3-CH₃ CH₃ Et1 CH₃ H 2-CH₃ 1 O O CH₃ 1927 E3 3-CH₃ H F 1 CH₃ H 2-CH₃ 1 O O CH₃ 1928E3 3-CH₃ F F 1 CH₃ H 2-CH₃ 1 O O CH₃ 1929 E3 3-CH₃ H CF₃ 1 CH₃ H 2-CH₃ 1O O CH₃ 1930 E3 3-CH₃ H c-Pr 1 CH₃ H 2-CH₃ 1 O O CH₃ 1931 E3 3-CH₃—CH2CH2— 1 CH₃ H 2-CH₃ 1 O O CH₃ 1932 E3 3-CH₃ —CH2CH2CH2— 1 CH₃ H 2-CH₃1 O O CH₃ 1933 E3 3-CH₃ —CH2CH(CH3)— 1 CH₃ H 2-CH₃ 1 O O CH₃ 1934 E33-CH₃ —CH2C(CH3)2— 1 CH₃ H 2-CH₃ 1 O O CH₃ 1935 E3 3-CH₃ H H 1 H H 2-CH₃1 O O CH₃ 1936 E3 3-CH₃ H H 1 Et H 2-CH₃ 1 O O CH₃ 1937 E3 3-CH₃ H H 1c-Pr H 2-CH₃ 1 O O CH₃ 1938 E3 3-CH₃ H H 1 CH═CH₂ H 2-CH₃ 1 O O CH₃ 1939E3 3-CH₃ H H 1 CH₂CH═CH₂ H 2-CH₃ 1 O O CH₃ 1940 E3 3-CH₃ H H 1 ethynyl H2-CH₃ 1 O O CH₃ 1941 E3 3-CH₃ H H 1 Propargyl H 2-CH₃ 1 O O CH₃ 1942 E33-CH₃ H H 1 CF₃ H 2-CH₃ 1 O O CH₃ 1943 E3 3-CH₃ H H 1 CH═CHCl H 2-CH₃ 1O O CH₃ 1944 E3 3-CH₃ H H 1 3,3,2-tri-Iodo-allyl H 2-CH₃ 1 O O CH₃ 1945E3 3-CH₃ H H 1 3-Iodopropargyl H 2-CH₃ 1 O O CH₃ 1946 E3 3-CH₃ H H 1 CNH 2-CH₃ 1 O O CH₃ 1947 E3 3-CH₃ H H 1 CN H 2-CH₃ 1 O O CH₃ 1948 E3 3-CH₃H H 1 NO₂ H 2-CH₃ 1 O O CH₃ 1949 E3 3-CH₃ H H 1 NH₂ H 2-CH₃ 1 O O CH₃1950 E3 3-CH₃ H H 1 NHCH₃ H 2-CH₃ 1 O O CH₃ 1951 E3 3-CH₃ H H 1 N(CH₃)₂H 2-CH₃ 1 O O CH₃ 1952 E3 3-CH₃ H H 1 CH₃ CH₃ 2-CH₃ 1 O O CH₃ 1953 E33-CH₃ H H 1 CH₃ Et 2-CH₃ 1 O O CH₃ 1954 E3 3-CH₃ H H 1 CH₃ CH₃CO 2-CH₃ 1O O CH₃ 1955 E3 3-CH₃ H H 1 CH₃ CH₃CH₂CO 2-CH₃ 1 O O CH₃ 1956 E3 3-CH₃ HH 1 CH₃ PhCO 2-CH₃ 1 O O CH₃ 1957 E3 3-CH₃ H H 1 CH₃ 4-Cl-PhCO 2-CH₃ 1 OO CH₃ 1958 E3 3-CH₃ H H 1 CH₃ PhCH₂CO 2-CH₃ 1 O O CH₃

TABLE 33 1959 E3 3-CH₃ H H 1 CH₃ CHO 2-CH₃ 1 O O CH₃ 1960 E3 3-CH₃ H H 1CH₃ CH₃OCH₂ 2-CH₃ 1 O O CH₃ 1961 E3 3-CH₃ H H 1 CH₃ CH₃CH(OCH₃) 2-CH₃ 1O O CH₃ 1962 E3 3-CH₃ H H 1 CH₃ CH₃SO₂ 2-CH₃ 1 O O CH₃ 1963 E3 3-CH₃ H H1 CH₃ PhSO₂ 2-CH₃ 1 O O CH₃ 1964 E3 3-CH₃ H H 1 CH₃ 4-CH₃-PhSO₂ 2-CH₃ 1O O CH₃ 1965 E3 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 S O CH₃ 1966 E3 3-CH₃ H H 1CH₃ H 2-CH₃ 1 O S CH₃ 1967 E3 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 O — CH₃ 1968 E33-CH₃ H H 1 CH₃ H 2-CH₃ 1 O NH CH₃ 1969 E3 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 ONCH₃ CH₃ 1970 E3 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O H 1971 E3 3-CH₃ H H 1 CH₃H 2-CH₃ 1 O O Et 1972 E3 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O n-Pr 1973 E33-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CH═CH₂ 1974 E3 3-CH₃ H H 1 CH₃ H 2-CH₃1 O O CH═CH₂ 1975 E3 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O Propargyl 1976 E33-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O ethynyl 1977 E3 3-CH₃ H H 1 CH₃ H 2-CH₃ 1O O CF₃ 1978 E3 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CF₃ 1979 E3 3-CH₃ H H 1CH₃ H 2-CH₃ 1 O O CF₂CF₃ 1980 E3 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CF₂CF₂H1981 E3 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O CH₂CH═CHCl 1982 E3 3-CH₃ H H 1 CH₃H 2-CH₃ 1 O O 3-Iodo-propargyl 1983 E3 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 O Oc-Pr 1984 E3 3-CH₃ H H 1 CH₃ H 2-CH₃ 1 O O c-Hex 1985 E3 3-CH₃ H H 1 CH₃H 2-CH₃ 1 O O 2-CH₃-c-Pr 1986 A1 — H H 2 CH₃ H 2-Cl 1 O O CH₃ 1987 A1 —H H 2 CH₃ H 2-CH₃ 1 O O CH₃

In addition, specific examples of the ketone derivative represented bythe aforementioned formula (II), which is an important key intermediatein the production of the oxime ether derivative of the presentinvention, are shown in the second tables (Tables 34 to 38).

(Second Tables)

TABLE 34 (II-1)

No R⁴ X n R⁵ Y Z R³ II-1 CH₃ — 0 H O O CH₃ II-2 H 2-Cl 1 H O O CH₃ II-3Et 2-Cl 1 H O O CH₃ II-4 CH₃ 2-Cl 1 H O O CH₃ II-5 CH═CH₂ 2-Cl 1 H O OCH₃ II-6 CH₂CH═CH₂ 2-Cl 1 H O O CH₃ II-7 ethynyl 2-Cl 1 H O O CH₃ II-8Propargyl 2-Cl 1 H O O CH₃ II-9 CF₃ 2-Cl 1 H O O CH₃ II-10 CH═CHCl 2-Cl1 H O O CH₃ II-11 3,3,2-tri-Iodo-allyl 2-Cl 1 H O O CH₃ II-123-Iodopropargyl 2-Cl 1 H O O CH₃ II-13 CN 2-Cl 1 H O O CH₃ II-14 NO₂2-Cl 1 H O O CH₃ II-15 NH₂ 2-Cl 1 H O O CH₃ II-16 NHCH₃ 2-Cl 1 H O O CH₃II-17 N(CH₃)₂ 2-Cl 1 H O O CH₃ II-18 CH₃ 2-Cl 1 CH₃ O O CH₃ II-19 CH₃2-Cl 1 Et O O CH₃ II-20 CH₃ 2-Cl 1 CH₃CO O O CH₃ II-21 CH₃ 2-Cl 1CH₃CH₂CO O O CH₃ II-22 CH₃ 2-Cl 1 PhCO O O CH₃

TABLE 35 No R⁴ X n R⁵ Y Z R³ II-23 CH₃ 2-Cl 1 4-Cl-PhCO O O CH₃ II-24CH₃ 2-Cl 1 PhCH₂CO O O CH₃ II-25 CH₃ 2-Cl 1 CHO O O CH₃ II-26 CH₃ 2-Cl 1CH₃OCH₂ O O CH₃ II-27 CH₃ 2-Cl 1 CH₃CH(OCH₃) O O CH₃ II-28 CH₃ 2-Cl 1CH₃SO₂ O O CH₃ II-29 CH₃ 2-Cl 1 PhSO₂ O O CH₃ II-30 CH₃ 2-Cl 14-CH₃-PhSO₂ O O CH₃ II-31 CH₃ 2-Cl 1 H S O CH₃ II-32 CH₃ 2-Cl 1 H O —CH₃ II-33 CH₃ 2-Cl 1 H O S CH₃ II-34 CH₃ 2-Cl 1 H O NH CH₃ II-35 CH₃2-Cl 1 H O NCH₃ CH₃ II-36 CH₃ 2-Cl 1 H O O H II-37 CH₃ 2-Cl 1 H O O EtII-38 CH₃ 2-Cl 1 H O O n-Pr II-39 CH₃ 2-Cl 1 H O O CH₂CH═CH₂ II-40 CH₃2-Cl 1 H O O CH═CH₂ II-41 CH₃ 2-Cl 1 H O O Propargyl II-42 CH₃ 2-Cl 1 HO O ethynyl II-43 CH₃ 2-Cl 1 H O O CF₃ II-44 CH₃ 2-Cl 1 H O O CH₂CF₃II-45 CH₃ 2-Cl 1 H O O CF₂CF₃ II-46 CH₃ 2-Cl 1 H O O CF₂CF₂H II-47 CH₃2-Cl 1 H O O CH₂CH═CHCl II-48 CH₃ 2-Cl 1 H O O 3-Iodo-propargyl II-49CH₃ 2-Cl 1 H O O c-Pr II-50 CH₃ 2-Cl 1 H O O c-Hex II-51 CH₃ 2-Cl 1 H OO 2-CH₃-c-Pr

TABLE 36 No R⁴ X n R⁵ Y Z R³ II-52 H 2-CH₃ 1 H O O CH₃ II-53 Et 2-CH₃ 1H O O CH₃ II-54 CH₃ 2-CH₃ 1 H O O CH₃ II-55 CH═C H₂ 2-CH₃ 1 H O O CH₃II-56 CH₂CH═CH₂ 2-CH₃ 1 H O O CH₃ II-57 ethynyl 2-CH₃ 1 H O O CH₃ II-58Propargyl 2-CH₃ 1 H O O CH₃ II-59 CF₃ 2-CH₃ 1 H O O CH₃ II-60 CH═CHCl2-CH₃ 1 H O O CH₃ II-61 3,3,2-tri-Iodo-allyl 2-CH₃ 1 H O O CH₃ II-623-Iodopropargyl 2-CH₃ 1 H O O CH₃ II-63 CN 2-CH₃ 1 H O O CH₃ II-64 NO₂2-CH₃ 1 H O O CH₃ II-65 NH₂ 2-CH₃ 1 H O O CH₃ II-66 NHCH₃ 2-CH₃ 1 H O OCH₃ II-67 N(CH₃)₂ 2-CH₃ 1 H O O CH₃ II-68 CH₃ 2-CH₃ 1 CH₃ O O CH₃ II-69CH₃ 2-CH₃ 1 Et O O CH₃ II-70 CH₃ 2-CH₃ 1 CH₃CO O O CH₃ II-71 CH₃ 2-CH₃ 1CH₃CH₂CO O O CH₃ II-72 CH₃ 2-CH₃ 1 PhCO O O CH₃ II-73 CH₃ 2-CH₃ 14-Cl-PhCO O O CH₃ II-74 CH₃ 2-CH₃ 1 PhCH₂CO O O CH₃ II-75 CH₃ 2-CH₃ 1CHO O O CH₃ II-76 CH₃ 2-CH₃ 1 CH₃OCH₂ O O CH₃ II-77 CH₃ 2-CH₃ 1CH₃CH(OCH₃) O O CH₃ II-78 CH₃ 2-CH₃ 1 CH₃SO₂ O O CH₃ II-79 CH₃ 2-CH₃ 1PhSO₂ O O CH₃ II-80 CH₃ 2-CH₃ 1 4-CH₃-PhSO₂ O O CH₃

TABLE 37 No R⁴ X n R⁵ Y Z R³ II-81 CH₃ 2-CH₃ 1 H S O CH₃ II-82 CH₃ 2-CH₃1 H O — CH₃ II-83 CH₃ 2-CH₃ 1 H O S CH₃ II-84 CH₃ 2-CH₃ 1 H O NH CH₃II-85 CH₃ 2-CH₃ 1 H O NCH₃ CH₃ II-86 CH₃ 2-CH₃ 1 H O O H II-87 CH₃ 2-CH₃1 H O O Et II-88 CH₃ 2-CH₃ 1 H O O n-Pr II-89 CH₃ 2-CH₃ 1 H O OCH₂CH═CH₂ II-90 CH₃ 2-CH₃ 1 H O O CH═CH₂ II-91 CH₃ 2-CH₃ 1 H O OPropargyl II-92 CH₃ 2-CH₃ 1 H O O ethynyl II-93 CH₃ 2-CH₃ 1 H O O CF₃II-94 CH₃ 2-CH₃ 1 H O O CH₂CF₃ II-95 CH₃ 2-CH₃ 1 H O O CF₂CF₃ II-96 CH₃2-CH₃ 1 H O O CF₂CF₂H II-97 CH₃ 2-CH₃ 1 H O O CH₂CH═CHCl II-98 CH₃ 2-CH₃1 H O O 3-Iodo-propargyl II-99 CH₃ 2-CH₃ 1 H O O c-Pr II-100 CH₃ 2-CH₃ 1H O O c-Hex II-101 CH₃ 2-CH₃ 1 H O O 2-CH₃-c-Pr II-102 H 2-Cl 1 H O Ot-Bu II-103 CH₃ 2-Cl 1 H O O t-Bu II-104 CF₃ 2-Cl 1 H O O t-Bu II-105CHF₂ 2-Cl 1 H O O CH₃ II-106 CHF₂ 2-Cl 1 H O O t-Bu II-107 CH₃ 2-F 1 H OO CH₃ II-108 CH₃ 2-F 1 H O O t-Bu II-109 CH₃ 2-Br 1 H O O t-Bu

TABLE 38 No R⁴ X n R⁵ Y Z R³ II-110 CH₃ 2-CHF₂ 1 H O O CH₃ II-111 CH₃2-CHF₂ 1 H O O t-Bu II-112 CH₃ 2-Cl-3-F 2 H O O CH₃ II-113 CH₃ 2-Cl-3-F2 H O O t-Bu

A compound of the present invention (oxime ether derivative representedby formula (I), or salt thereof) demonstrates superior bactericidalaction against a wide range of types of fungi, such as fungi belongingto Oomycetes, Ascomycetes Deuteromycetes and Basidiomycetes. Thus, aswill be described later, oxime ether derivative compounds of the presentinvention are useful as active ingredients of fungicides foragricultural and horticultural use.

2) Fungicide for Agricultural and Horticultural Use

A second aspect of the present invention is a fungicide for agriculturaland horticultural use containing at least one of an oxime etherderivative of the present invention represented by formula (I), or asalt thereof (to be referred to as the “fungicide of the presentinvention”).

The fungicide of the present invention contains an oxime etherderivative of the present invention or salt thereof as an activeingredient thereof, and has superior bactericidal action against a widerange of types of fungi, such as fungi belonging to Oomycetes,Ascomycetes Deuteromycetes and Basidiomycetes.

The fungicide of the present invention can be used to control variousplant diseases occurring during cultivation of agricultural andhorticultural crops such as flowering plants, lawn grasses and pasturegrasses by seed treatment, foliar spraying, soil application or watersurface application and the like.

Examples of crops in which plant diseases can be controlled along withtheir plant diseases and causative organisms include:

Sugar Beets:

-   -   Cercospora leaf spot (Cercospora beticola)

Peanuts:

-   -   Brown leaf spot (Mycosphaerella arachidis)    -   Black leaf blight (Mycosphaerella berkeleyi)

Cucumbers:

-   -   Powdery mildew (Sphaerotheca fuliginea)    -   Gummy stem blight (Mycosphaerella melonis)    -   Sclerotinia rot (Sclerotinia sclerotiorum)    -   Gray mold (Botrytis cinerea)    -   Scab (Cladosporium cucumerinum)    -   Corynespora leaf spot (Corynespora cassicola)    -   Damping-off (Pythium debaryanam, Rhizoctonia solani Kuhn)    -   Bacterial spot (Pseudomonas syringae pv. Lecrymans)

Tomatoes:

-   -   Gray mold (Botrytis cinerea)    -   Leaf mold (Cladosporium fulvum)

Eggplants:

-   -   Gray mold (Botrytis cinerea)    -   Black rot (Corynespora malongenae)    -   Powdery mildew (Erysiphe cichoracearum)    -   Leaf mold (Mycovellosiella nattrassii)

Strawberries:

-   -   Gray mold (Botrytis cinerea)    -   Powdery mildew (Sphaerotheca humuli)    -   Anthracnose (Colletotrichum acutatum, Colletotrichum fragariae)

Onions:

-   -   Neck rot (Botrytis allii)    -   Gray mold (Botrytis cinerea)    -   Leaf blight (Botrytis squamosa)

Cabbage:

-   -   Clubroot (Plasmodiophora brassicae)    -   Bacterial soft rot (Erwinia carotovora)

Kidney beans:

-   -   Stem rot (Sclerotinia sclerotiorum)    -   Gray mold (Botrytis cinerea)

Apples:

-   -   Powdery mildew (Podosphaera leucotricha)    -   Scab (Venturia inaequalis)    -   Blossom blight (Monilinia mali)    -   Valsa canker (Valsa mali)    -   Alternaria blotch (Alternaria mali)    -   Rust (Gymnosporangium yamadae)    -   Ring rot (Botryosphaeria berengeriana)    -   Anthracnose (Coletotrichum gloeosprioides)    -   Blotch (Diplocarpon mali)

Persimmons:

-   -   Powdery mildew (Phyllactinia kakicola)    -   Anthracnose (Gloeosporium kaki)    -   Angular leaf spot (Cercospora kaki)

Peaches and cherries:

-   -   Brown rot (Monilinia fructicola)

Grapes:

-   -   Gray mold (Botrytis cinerea)    -   Powdery mildew (Uncinula necator)    -   Ripe rot (Glomerella cingulata)

Pears:

-   -   Scab (Venturia nashicola)    -   Rust (Gymnosporangium asiaticum)    -   Black spot (Alternaria kikuchiana)

Tea:

-   -   Gray blight (Pestalotia theae)    -   Anthracnose (Collectotrichum theae-sinensis)

Citrus:

-   -   Scab (Elsinoe fawcette)    -   Blue mold (Penicillium italicum)    -   Common green mold (Penicillium digitatum)    -   Gray mold (Botrytis cinerea)    -   Melanose (Diaporthe citri)    -   Canker (Xanthomonas campestris pv. Citri)

Wheat:

-   -   Powdery mildew (Erysiphe graminis f. sp. tritici)    -   Fusarium blight (Gibberella zeae)    -   Leaf rust (Puccinia recondita)    -   Browning root rot (Pythium iwayamai)    -   Snow mold (Monographella nivalis)    -   Eye spot (Pseudocercosporella herpotrichoides)    -   Speckled leaf blotch (Septoria tritici)    -   Glume blotch (Leptosphaeria nodorum)    -   Typhula snow blight (Typhula incarnata)    -   Sclerotinia snow blight (Myriosclerotinia borealis)    -   Take-all (Gaeumanomyces graminis)

Barley:

-   -   Stripe (Pyrenophora graminea)    -   Leaf blotch (Rhynchosporium secalis)    -   Loose smut (Ustilago tritici, U. nuda)

Rice:

-   -   Blast (Pyricularia oryzae)    -   Sheath blight (Rhizoctonia solani)    -   Bakanae disease (Gibberella fujikuroi)    -   Brown spot (Cochliobolus niyabeanus)

Tobacco:

-   -   Sclerotinia stem-rot (Sclerotinia sclerotiorum)    -   Powdery mildew (Erysiphe cichoracearum)

Tulips:

-   -   Gray mold (Botrytis cinerea)

Bent grass:

-   -   Sclerotinia snow blight (Sclerotinia borealis)

Orchard grass:

-   -   Powdery mildew (Erysiphe graminis)

Soybeans:

-   -   Purple stain (Cercospora kikuchii)

Potatoes, tomatoes:

-   -   Late blight (Phytophthora infestans)

Cucumbers:

-   -   Downy mildew (Pseudoperonospora cubensis)

Grapes:

-   -   Downy mildew (Plasmopara viticola)

In addition, various pathogens have recently developed resistance tobenzimidazole fungicides and dicarboximide fungicides resulting ininadequate efficacy of these drugs, thereby creating the need foreffective drugs against resistant organisms as well. The fungicide ofthe present invention also has superior bactericidal effects againstresistant organisms in addition to pathogens that are sensitive to thesedrugs.

For example, the fungicide of the present invention is effective againstgray mold (Botrytis cinerea), sugar beet cercospora leaf spot(Cercospora beticola) and apple scab (Venturia inaequalis), pear scab(Venturia nashicola), which exhibit resistance to benzimidazolefungicides such as thiophanate-methyl, benomyl, carbendazim andthiabendazole, in the same manner as sensitive organisms.

Moreover, the fungicide of the present invention is effective againstgray mold (Botrytis cinerea), which exhibits resistance to dicarboximidefungicides (such as vinclozoline, procymidone and iprodione) in the samemanner as sensitive organisms.

Examples of diseases for which application of the fungicide of thepresent invention is more preferable include sugar beet cercospora leafspot, wheat powdery mildew, rice blast, apple scab, cucumber gray moldand peanut brown leaf spot.

In addition, the fungicide of the present invention causes littlechemical damage, exhibits low toxicity to fish and warm-blooded animals,and has a high degree of safety.

During actual use of the fungicide of the present invention, the oximeether derivative compound of the present invention may be used in pureform without adding other components, or may be used in the form able tobe adopted by an ordinary agricultural chemical for the purpose of usingas an agricultural chemical, namely in the form of an agriculturalchemical preparation such as a wettable powder, granules, powder,emulsion, aqueous solution, suspension or water-dispersible granules.

Examples of additives and carriers able to be added to the agriculturalchemical preparation used for the purpose of solid formulations includevegetable powders such as soybean powder or wheat powder, mineral finepowders such as diatomaceous earth, apatite, gypsum, talc, bentonite,pyrophyllite or clay, and organic and inorganic compounds such as sodiumbenzoate, urea or sodium sulfate.

In addition, in the case of using for the purpose of liquidformulations, kerosene, xylene and petroleum-based aromatichydrocarbons, cyclohexane, cyclohexanone, dimethylformamide,dimethylsulfoxide, alcohol, acetone, trichloroethylene, methyl isobutylketone, mineral oil, vegetable oil and water, for example, can be usedas solvents.

Moreover, a surfactant can be added to these preparations as necessaryto obtain a uniform and stable form.

There are no particular limitations on surfactants that can be added,and examples include nonionic surfactants such as polyoxyethylene-alkylphenyl ethers, polyoxyethylene-alkyl ethers, polyoxyethylene-higherfatty acid esters, polyoxyethylene-sorbitan fatty acid esters orpolyoxyethylene-tristyryl phenyl ether, and sulfuric acid ester salts ofpolyoxyethylene-alkyl phenyl ethers, alkyl benzene sulfonates, sulfuricacid ester salts of higher alcohols, alkyl naphthalene sulfonates,polycarboxylates, lignin sulfonates, formaldehyde condensates of alkylnaphthalene sulfonates and isobutylene-maleic anhydrate copolymers.

Wettable powders, emulsions, flowable agents, aqueous solutions andwater-dispersible granules are used in the form of solutions,suspensions or emulsions by diluting to a prescribed concentration withwater, while powders and granules are used by spraying directly ontoplants.

Normally, the amount of active ingredient in the fungicide of thepresent invention is preferably 0.01 to 90% by weight and morepreferably 0.05 to 85% by weight based on the total weight of thecomposition (preparation).

Although the applied amount of the fungicide of the present inventionvaries according to weather conditions, preparation form, applicationtime, application method, applied location, target control disease,target crop and the like, it is normally 1 to 1,000 g and preferably 10to 100 g as the amount of active ingredient compound per hectare.

In the case of applying by diluting a wettable powder, emulsion,suspension, aqueous solutions and water-dispersible granules with water,the applied concentration is 1 to 1000 ppm and preferably 10 to 250 ppm.

In addition to the oxime ether derivative compound of the presentinvention, the fungicide of the present invention can also be mixed withone or two or more of various fungicides, insecticides, miticides orsynergists.

Typical examples of fungicides, insecticides, miticides and plant growthregulators able to be used by mixing with the oxime ether derivativecompound of the present invention are indicated below.

Fungicides:

-   -   captan, folpet, thiuram, ziram, zineb, maneb, mancozeb,        propineb, polycarbamate, chlorothalonil, quintozene, captafol,        iprodione, procymidone, vinclozolin, fluoroimide, cymoxanil,        mepronil, flutolanil, pencycuron, oxycarboxin, fosetyl-aluminum,        propamocarb, triadimefon, triadimenol, propiconazole,        diclobutorazol, bitertanol, hexaconazol, miclobutanil,        flusilazole, metconazole, etaconazole, fluotrimazole,        cyproconazole, epoxyconazole, flutriafen, penconazole,        diniconazole, cyproconazole, fenarimol, triflumizole,        prochloraz, imazalil, pefurazoate, tridemorph, fenpropimorph,        triforine, buthiobate, pyrifenox, anilazine, polyoxin,        metalaxyl, oxadixyl, furalaxyl, isoprothiolane, probenazole,        pyrrolnitrin, blasticidin S, kasugamycin, validamycin,        dihydrostreptomycin sulfate, benomyl, carbendazim,        thiophanate-methyl, hymexazol, basic copper chloride, basic        copper sulfate, fentin acetate, triphenyltin hydroxide,        diethofencarb, methasulfocarb, qinomethionate, binapacryl,        lecithin, sodium bicarbonate, dithianon, dinocap, fenaminosulf,        diclomezine, guazatine, dodine, IBP, edifenphos, mepanipyrim,        ferimzone, trichlamide, methasulfocarb, fluazinam, ethoqinolac,        dimethomorph, pyroquilon, tecloftalam, fthalide, phenazine        oxide, thiabendazole, tricyclazole, vinclozolin, cymoxanil,        cyclobutanil, guazatine, propamocarb hydrochloride, oxolinic        acid, hydroxyisoxazole, iminoctadine acetate, and the like.

Insecticides/Miticides:

Organic phosphorous and carbamate-based insecticides:

-   -   fenthion, fenitrothion, diazinon, chlorpyrifos, ESP,        vamidothion, phenthoate, dimethoate, formothion, malathion,        trichlorfon, thiometon, phosmet, dichlorvos, acephate, EPBP,        methyl parathion, oxydemetone methyl, ethion, salithion,        cyanophos, isoxathion, pyridafenthion, phosalone, methidathion,        sulprofos, chlorfenvinphos, tetrachlorovinphos, dimethylvinphos,        propaphos, isofenphos, ethyl thiometon, profenofos, pyraclofos,        monocrotophos, azinphos-methyl, aldicarb, methomyl, thiodicarb,        carbofuran, carbosulphan, benfuracarb, furathiocarb, propoxur,        BPMC, MTMC, MIPC, carbaryl, pirimicarb, ethiophencarb,        phenoxycarb, EDDP, and the like.    -   Pyrethroid-based insecticides: permethrin, cypermethrin,        deltamethrin, fenvalerate, fenpropathrin, pyrethrin, allethrin,        tetramethrin, resmethrin, dimethrin, propathrin, phenothrin,        prothrin, fluvalinate, cyfluthrin, cyhalothrin, flucythrinate,        etofenprox, cycloprothrin, tralomethrin, silafluofen,        flufenprox, acrinathrin, and the like.    -   Benzoylurea-based and other insecticides: diflubenzuron,        chlorfluazuron, hexaflumuron, triflumuron, tetrabenzuron,        flufenoxuron, flucycloxuron, buprofezin, pyriproxyfen,        methoprene, benzoepin, diafenthiuron, acetamiprid, imidacloprid,        nitenpyram, fipronil, cartap, thiocyclam, bensultap, nicotine        sulfate, rotenone, metaldehyde, machine oil, BT and microbial        agrichemicals such as insect pathogenic viruses.

Nematocides:

-   -   Fenamiphos, fosthiazate, and the like

Miticides:

-   -   Chlorobenzilate, phenisobromolate, dicofol, amitraz, BPPS,        benzomate, hexythiazox, fenbutatin oxide, polynactin,        chinomethionate, CPCBS, tetradifon, avermectin, milbemectin,        clofentezine, cyhexatin, pyridaben, fenpyroximate, tebufenpyrad,        pyrimidifen, fenothiocarb, dienochlor, and the like.

Plant growth regulators:

-   -   Gibberellins (such as gibberellin A3, gibberellin A4 or        gibberellin A7), IAA, NAA, and the like.

EXAMPLES

Although the following provides a more detailed explanation of thepresent invention through examples thereof, the present invention is notlimited to the following examples.

Example 1 (1) Production of t-Butyl N-(5-bromo-2-chlorophenoxy)Carbamate

12.34 g of potassium hydroxide were added to a solution in which 5.00 gof 4-bromo-1-chloro-3-fluorobenzene and 4.14 g of N-(t-butoxycarbonyl)hydroxylamine were dissolved in 50 ml of dimethylsulfoxide at roomtemperature followed by stirring for 2 hours at 60° C. After cooling toroom temperature, the reaction solution was poured into ice water andextracted with ethyl acetate. The ethyl acetate layer was washed threetimes with water followed by drying by addition of anhydrous magnesiumsulfate, filtering and distilling off the solvent from the filtrateunder reduced pressure. The resulting residue was purified by silica gelcolumn chromatography (developing solvent; n-hexane:ethyl acetate=5:1(volume ratio)) to obtain 7.39 g of the target compound of t-butylN-(5-bromo-2-chlorophenoxy) carbamate (yield: 96%).

[¹H-NMR Data of t-Butyl N-(5-bromo-2-chlorophenoxy) Carbamate]

¹H-NMR (CDCl₃/TMS, δ ppm): 7.60 (bs, 1H), 7.47 (d, 1H), 7.20 (d, 1H),7.10 (dd, 1H), 1.52 (s, 9H)

(2) Production of t-Butyl N-(5-acetyl-2-chlorophenoxy) Carbamate

500 ml of THF were cooled to −78° C. in a nitrogen atmosphere followedby the addition of 198 ml of n-butyllithium (2.77 mol/L). A solutioncontaining 67.43 g of t-butyl N-(5-bromo-2-chlorophenoxy) carbamatedissolved in 170 ml of THF was dropped therein followed by stirring for10 minutes at −78° C. following completion of dropping. Next, 54.63 g ofN,N-dimethylacetamide were dropped in followed by stirring for 1 hour at−78° C. following completion of dropping. Following completion of thereaction, an aqueous ammonium chloride solution was added at −78° C. toterminate the reaction followed by extraction with ethyl acetate. Afterdrying the ethyl acetate layer by addition of anhydrous magnesiumsulfate and filtering, the solvent was distilled off from the filtrateunder reduced pressure. The resulting residue was purified by silica gelcolumn chromatography (developing solvent; n-hexane:ethyl acetate=3:1(volume ratio)) to obtain 29.18 g of the target compound of t-butylN-(5-acetyl-2-chlorophenoxy) carbamate in the form of crystals (yield:49%).

Melting point: 120 to 123° C.

(3) Production of Methyl N-(5-acetyl-2-chlorophenoxy) Carbamate

15.37 g of triethylamine were added to a solution containing 28.93 g oft-butyl N-(5-acetyl-2-chlorophenoxy) carbamate dissolved in 380 ml ofmethylene chloride while cooling with ice. Next, 12.44 g of methylchloroformate were dropped into this mixture followed by stirring for 1hour at room temperature following completion of dropping. Followingcompletion of the reaction, water was added to the reaction liquid whilecooling with ice to separate the methylene chloride layer. After dryingthe methylene chloride layer by addition of anhydrous magnesium sulfateand filtering, the solvent was distilled off from the filtrate underreduced pressure.

250 ml of methylene chloride were added to the resulting residue and 64ml of trifluoroacetic acid were dropped in while cooling with icefollowed by stirring for 1.5 hours at room temperature followingcompletion of dropping. Following completion of the reaction, thereaction liquid was transferred to a saturated aqueous sodiumbicarbonate solution and extracted with methylene chloride. After dryingthe methylene chloride layer by addition of anhydrous magnesium sulfateand filtering, the solvent was distilled off from the filtrate underreduced pressure to obtain a crude product. The resulting crude productwas then washed with n-hexane to obtain 23.28 g of the target compoundof methyl N-(5-acetyl-2-chlorophenoxy) carbamate in the form of crystals(yield: 94%).

Melting point: 154 to 155° C.

(4) Production of (6-Trifluoromethylpyridin-2-yl) Methanol

A solution containing 2.00 g of 2-bromo-6-trifluoromethylpyridinedissolved in 50 ml of toluene was cooled to −78° C. followed by droppingin 4.0 ml of n-butyllithium (2.77 mol/L) and stirring for 10 minutes at−78° C. 0.96 g of N,N-dimethylformamide were dropped therein followed byfurther stirring for 10 minutes at −78° C. following completion of thereaction. 0.67 g of sodium borohydride and 5 ml of methanol were addedto the resulting reaction mixture followed by heating to roomtemperature and stirring for 1 hour at room temperature. Followingcompletion of the reaction, aqueous ammonium chloride solution was addedto the reaction liquid followed by extraction with ethyl acetate. Theethyl acetate layer was dried by addition of anhydrous magnesium sulfatefollowed by filtering and distilling off the solvent from the filtrateunder reduced pressure to obtain 1.70 g of a crude product in the formof (6-trifluoromethylpyridin-2-yl) methanol.

[¹H-NMR Data of (6-Trifluoromethylpyridin-2-yl) Methanol]

¹H-NMR (CDCl₃/TMS, δ ppm): 7.88 (dd, 1H), 7.60 (d, 1H), 7.50 (d, 1H),4.85 (s, 2H), 3.36 (bs, 1H)

(5) Production of t-Butyl N-[(6-trifluoromethylpyridin-2-yl)methoxy]Carbamate

3.78 g of carbon tetrabromide and 2.78 g of triphenylphosphine wereadded to a solution containing 1.70 g of the(6-trifluoromethylpyridin-2-yl) methanol obtained in (4) dissolved in 30ml of methylene chloride followed by stirring for 1 hour at roomtemperature. 30 ml of acetonitrile, 1.52 g of N-(t-butoxycarbonyl)hydroxylamine and 1.74 g of 1,8-diazabicyclo[5.4.0]-7-undecene (DBU)were added to this reaction solution followed by stirring for 3 hours atroom temperature. Following completion of the reaction, aqueous ammoniumchloride solution was added to the reaction mixture followed byextraction with ethyl acetate. The ethyl acetate layer was dried byaddition of anhydrous magnesium sulfate followed by filtration anddistilling off the solvent from the filtrate under reduced pressure. Theresulting residue was purified by silica gel column chromatography(developing solvent; n-hexane:ethyl acetate=3:1 (volume ratio)) toobtain 1.54 g of the target compound of t-butylN-[(6-trifluoromethylpyridin-2-yl)methyloxy] carbamate (yield: 59%).

[¹H-NMR Data of t-Butyl N-[(6-trifluoromethylpyridin-2-yl)methyloxy]Carbamate

¹H-NMR (CDCl₃/TMS, δ ppm): 7.90 (dd, 1H), 7.73 (d, 1H), 7.62 (d, 1H),7.44 (bs, 1H), 1.48 (s, 9H)

(6) Production of MethylN-(2-chloro-5-{1-[6-fluoromethyl-pyridin-2-ylmethoxyimino]ethyl}phenoxy)Carbamate

A mixture of 0.30 g of methyl N-(5-acetyl-2-chlorophenoxy) carbamate and0.47 g of t-butyl N-[(6-trifluoromethylpyridin-2-yl)methyloxy] carbamatewas dissolved in 15 ml of dichloroethane. 1 ml of trifluoroacetic acidwas added to this solution followed by stirring for 1 hour at 50° C.Following completion of the reaction, ethyl acetate was added to thereaction mixture followed by washing with saturated aqueous sodiumbicarbonate solution to separate the organic layer. The resultingorganic layer was dried by addition of anhydrous magnesium sulfatefollowed by filtering and distilling off the solvent from the filtrateunder reduced pressure. The resulting residue was purified by silica gelcolumn chromatography (developing solvent; n-hexane:ethyl acetate=3:1(volume ratio)) to obtain 0.44 g of the target compound of methylN-(2-chloro-5-{1-[6-trifluoromethylpyridin-2-ylmethoxyimino]ethyl}phenoxy)carbamate in the form of crystals (yield: 86%)

Melting point: 100 to 101° C.

Melting point, refractive index and NMR data for oxime ether derivativecompounds of the present invention produced in the same manner asExample 1 are shown in the following third tables (Tables 39 and 40). Inthe tables, No. indicates the compound number shown in the first table,while NMR indicates values measured in chloroform-d using TMS for thestandard.

(Third Tables)

TABLE 39 Melting Point No. (° C.) NMR 3 100-102 4 7.87 (s, 1H), 7.66 (d,1H), 7.35 (d, 1H), 7.29 (dd, 1H), 6.87 (s, 1H), 5.46 (s, 2H), 3.85 (s,3H), 2.82 (q, 2H), 2.26 (s, 3H), 1.30 (t, 3H) 5 108-109 28 101-103 52141-143 93 7.81 (bs, 1H), 7.52 (d, 1H), 7.23 (dd, 1H), 7.12 (d, 1H),6.86 (s, 1H), 5.46 (s, 2H), 3.82 (s, 3H), 2.64 (q, 2H), 2.27 (s, 3H),2.26 (s, 3H), 1.28 (t, 3H) 94 65-67 727 108-109 1434 109-111 1434130-132 1437 98-99 1438 87-89 1444 143-145 1445 120-122 1446 100-1011448 130-131

TABLE 40 Melting Refractive No. Point (° C.) Index NMR 1462 7.75 (s,1H), 7.55-7.60 (m, 2H), 7.25-7.31 (m, 2H), 7.14 (d, 1H), 7.04 (d, 1H),5.44 (q, 1H), 3.83 (s, 3H), 2.82 (q, 2H), 2.30 (s, 3H), 1.63 (d, 3H),1.30 (t, 3H), 1.63 (d, 3H) 1463 7.76 (s, 1H), 7.63 (dd, 1H), 7.55 (d,1H), 7.20-7.32 (m, 4H), 5.42 (q, 1H), 3.83 (s, 3H), 2.30 (s, 3H), 1.63(d, 3H) 1464 nD1.5241 (22.9° C.) 1465 nD1.5426   (23° C.) 1539 82-841555 7.99 (bs, 1H), 7.56 (t, 1H), 7.42 (d, 1H), 7.18-7.14 (m, 2H), 7.06(d, 1H), 7.02 (d, 1H), 5.44 (q, 1H), 3.79 (s, 3H), 2.81 (q, 2H), 2.29(s, 3H), 2.24 (s, 3H), 1.62 (d, 3H), 1.29 (t, 3H) 1619 118-120 1622121-123

Physical properties or NMR data of ketone derivatives (compoundsrepresented by formula (II)) produced in the same manner as Example 1are shown in the following fourth table (Table 41).

TABLE 41 Physical No. Property (° C.) NMR II-4 m.p. 154-155 II-9 ¹H-NMR(CDCl₃)/TMS, δ (ppm): 8.01 (d, 1H), 7.95 (s, 1H), 7.69 (dd, 1H), 7.54(d, 1H), 3.86 (s, 3H) II-54 ¹H-NMR (CDCl₃)/TMS, δ (ppm): 7.79 (d, 1H),7.73 (s, 1H), 7.54 (dd, 1H), 7.21 (d, 1H), 3.84 (s, 3H), 2.57 (s, 3H),2.32 (s, 3H) II-102 ¹H-NMR (CDCl₃)/TMS, δ (ppm): 9.95 (s, 1H), 7.84 (d,1H), 7.66 (s, 1H), 7.55-7.48 (m, 2H), 1.52 (s, 9H) II-103 m.p. 120-123II-104 ¹H-NMR (CDCl₃)/TMS, δ (ppm): 8.00 (d, 1H), 7.74-7.66 (m, 2H),7.53 (d, 1H), 1.52 (s, 9H) II-105 ¹H-NMR (CDCl₃)/TMS, δ (ppm): 8.00 (d,1H), 7.88 (s, 1H), 7.73 (dd, 1H), 7.52 (d, 1H), 6.25 (t, 1H), 3.86 (s,3H) II-106 ¹H-NMR (CDCl₃)/TMS, δ (ppm): 8.00 (d, 1H), 7.72-7.69 (m, 2H),7.51 (d, 1H), 6.25 (t, 1H), 1.52 (s, 9H) II-107 ¹H-NMR (CDCl₃)/TMS, δ(ppm): 7.95 (dd, 1H), 7.85 (s, 1H), 7.67-7.62 (m, 1H), 7.17 (dd, 1H),3.86 (s, 3H), 2.58 (s, 3H) II-108 ¹H-NMR (CDCl₃)/TMS, δ (ppm): 7.95 (dd,1H), 7.68 (s, 1H), 7.65-7.60 (m, 1H), 7.16 (dd, 1H), 2.58 (s, 3H), 1.51(s, 9H) II-109 ¹H-NMR (CDCl₃)/TMS, δ (ppm): 7.86 (d, 1H), 7.86 (s, 1H),7.61 (d, 1H), 7.48 (dd, 1H), 2.59 (s, 3H), 1.52 (s, 9H) II-110 ¹H-NMR(CDCl₃)/TMS, δ (ppm): 7.91 (s, 1H), 7.86 (s, 1H), 7.69 (s, 2H), 7.01 (t,1H), 3.84 (s, 3H), 2.62 (s, 3H) II-111 ¹H-NMR (CDCl₃)/TMS, δ (ppm): 7.91(bs, 2H), 7.68 (bs, 2H), 7.04 (t, 1H), 2.62 (s, 3H), 1.52 (s, 9H) II-112¹H-NMR (CDCl₃)/TMS, δ (ppm): 7.89 (s, 1H), 7.72 (dd, 1H), 7.44 (dd, 1H),3.86 (s, 3H), 2.58 (s, 3H) II-113 ¹H-NMR (CDCl₃)/TMS, δ (ppm): 7.72 (d,1H), 7.69 (s, 1H), 7.42 (dd, 1H), 2.58 (s, 3H), 1.52 (s, 9H)

Although the following indicates some examples of the fungicide of thepresent invention, the additives and addition ratios are not limited tothose indicated in the examples and can be varied over a wide range. Inaddition, the term “parts” in the preparation examples indicates partsby weight.

Preparation Example 1 Wettable Powder

Oxime ether derivative compound of 40 parts present invention Clay 48parts Sodium dioctylsulfosuccinate  4 parts Sodium lignin sulfonate  8parts

The above components are uniformly mixed and finely crushed to obtain awettable powder containing 40% of the active ingredient.

Preparation Example 2 Emulsion

Oxime ether derivative compound of 10 parts present invention Solvesso200 53 parts Cylohexanone 26 parts Calcium dodecylbenzenesulfonate  1part Polyoxyethylene alkyl allyl ether 10 parts

The above components are mixed and dissolved to obtain an emulsioncontaining 10% of the active ingredient.

Preparation Example 3 Powder

Oxime ether derivative compound of 10 parts present invention Clay 90parts

The above components are uniformly mixed and finely crushed to obtain apowder containing 10% of the active ingredient.

Preparation Example 4 Granules

Oxime ether derivative compound of 5 parts present invention Clay 73parts Bentonite 20 parts Sodium dioctylsulfosuccinate 1 part Potassiumphosphate 1 part

The above components are finely crushed and mixed well followed by theaddition of water, mixing well, granulating and drying to obtaingranules containing 5% of the active ingredient.

Preparation Example 5 Suspension

Oxime ether derivative compound of 10 parts present inventionPolyoxyethylene alkyl allyl ether 4 parts Sodium polycarbonate 2 partsGlycerin 10 parts Xanthan gum 0.2 parts Water 73.8 parts

The above components are mixed followed by wet-crushing to a particlediameter of 3 microns or less to obtain a suspension containing 10% ofthe active ingredient.

Preparation Example 6 Water Dispersible Granules

Oxime ether derivative compound of 40 parts present invention Clay 36parts Potassium chloride 10 parts Sodium alkylbenzenesulfonate 1 partSodium lignin sulfonate 8 parts Formaldehyde condensation product of 5parts sodium alkylbenzenesulfonate

The above components are uniformly mixed and finely crushed followed byadding a suitable amount of water and mixing to form a clay-likemixture. The clay-like mixture is granulated and dried to obtain waterdispersible granules containing 40% of the active ingredient.

The following indicates test examples of fungicides of the presentinvention obtained in the manner described above.

Test Example 1 Apple Scab Control Test

Emulsions of oxime ether derivative compounds of the present inventionwere sprayed at an active ingredient concentration of 100 ppm onto appleseedlings (variety: Ralls Janet, leaf stage: 3 to 4) cultivated inunglazed pots. After allowing to air-dry at room temperature, theseedlings were inoculated with conidiospores of apple scab pathogen(Venturia inaequalis) followed by holding for 2 weeks indoors at 20° C.and high humidity using a 12 hour light/dark cycle. The appearance oflesions on the leaves was compared with untreated seedlings to determinecontrol effects.

As a result, the following compounds demonstrated superior controlvalues of 75% or more:

compound numbers (compound numbers correspond to compound numbers listedin the above-mentioned first tables, and to apply similarlyhereinafter): 3, 4, 5, 28, 52, 93, 94, 727, 1434, 1437, 1438, 1444,1445, 1446, 1448, 1462, 1463, 1464, 1465, 1539, 1555, 1619, 1622, 1803.

Test Example 2 Wheat Powdery Mildew Control Test

Wettable powders of oxime ether derivative compounds of the presentinvention were sprayed at a concentration of 100 ppm onto wheatseedlings (variety: Chihoku, leaf stage: 1.0 to 1.2) cultivated inunglazed pots. After allowing the leaves to air-dry, the leaves wereshake-inoculated with conidiospores of wheat powdery mildew pathogen(Erysiphe graminis f. sp. tritici) and held for 7 days in a greenhouseat 22 to 25° C. The appearance of lesions on the leaves was comparedwith untreated seedlings to determine control effects.

As a result, the following compounds demonstrated superior controlvalues of 75% or more:

compound numbers: 3, 4, 5, 28, 93, 94, 727, 1434, 1437, 1438, 1444,1445, 1446, 1448, 1462, 1463, 1539, 1555.

Test Example 3 Wheat Leaf Rust Control Test

Wettable powders of oxime ether derivative compounds of the presentinvention were sprayed at a concentration of 100 ppm onto wheatseedlings (variety: Norin 61, leaf stage: 1.0 to 1.2) cultivated inunglazed pots. After allowing the leaves to air-dry, the leaves wereshake-inoculated with urediospores of wheat rust pathogen (Pucciniarecondita) and held for 10 days in a greenhouse at 22 to 25° C. Theappearance of lesions on the leaves was compared with untreatedseedlings to determine control effects.

As a result, the following compounds demonstrated superior controlvalues of 75% or more:

compound numbers: 3, 4, 5, 28, 93, 94, 727, 1437, 1438, 1444, 1445,1446, 1448, 1462, 1463, 1464, 1539, 1555, 1803.

1. An oxime ether derivative represented by the following formula (I),or a salt thereof:

wherein, X represents a halogen atom, C₁₋₂₀ alkyl group, C₁₋₂₀ alkoxygroup, C₁₋₂₀ haloalkyl group or C₁₋₂₀ haloalkoxy group, R¹ and R² eachindependently represent a hydrogen atom, halogen atom, C₁₋₂₀ alkylgroup, C₁₋₂₀ haloalkyl group, optionally substituted C₃₋₁₀ cycloalkylgroup, or R¹ and R² may bond together to form a ring, R³ represents ahydrogen atom, C₁₋₂₀ alkyl group, C₂₋₂₀ alkenyl group, C₂₋₂₀ alkynylgroup, C₁₋₂₀ haloalkyl group, C₂₋₂₀ haloalkenyl group, C₂₋₂₀ haloalkynylgroup or optionally substituted C₃₋₁₀ cycloalkyl group; R⁴ represents ahydrogen atom, C₁₋₂₀ alkyl group, optionally substituted C₃₋₁₀cycloalkyl group, C₂₋₂₀ alkenyl group, C₂₋₂₀ alkynyl group, C₁₋₂₀haloalkyl group, C₂₋₂₀ haloalkenyl group, C₂₋₂₀ haloalkynyl group, cyanogroup, nitro group or optionally substituted amino group, R⁵ representsa hydrogen atom, C₁₋₂₀ alkyl group, acyl group, formyl group, C₁₋₂₀alkoxy-C₁₋₂₀ alkyl group, C₂₋₂₀ acyloxy-C₁₋₂₀ alkyl group, C₁₋₂₀alkoxycarbonyl group, C₁₋₂₀ alkylsulfonyl group or optionallysubstituted phenylsulfonyl group, Y represents an oxygen atom or sulfuratom, Z represents a single bond, oxygen atom, sulfur atom or NR⁶(wherein, R⁶ represents a hydrogen atom or C₁₋₃₀ alkyl group), Hetrepresents an optionally substituted heterocyclic group, m represents aninteger of 1 to 8, and R¹ and R² may be the same or different in thecase m is 2 or more, and n represents an integer of 0 to 4, and X may bethe same or different in the case n is 2 or more.
 2. A fungicide foragricultural and horticultural use that contains at least one of theoxime ether derivative according to claim 1, or salt thereof, as anactive ingredient thereof.
 3. A ketone derivative represented by thefollowing formula (II):

wherein, X represents a halogen atom, C₁₋₂₀ alkyl group, C₁₋₂₀ alkoxygroup, C₁₋₂₀ haloalkyl group or C₁₋₂₀ haloalkoxy group, R³ represents ahydrogen atom, C₁₋₂₀ alkyl group, C₂₋₂₀ alkenyl group, C₂₋₂₀ alkynylgroup, C₁₋₂₀ haloalkyl group, C₂₋₂₀ haloalkenyl group, C₂₋₂₀ haloalkynylgroup or optionally substituted C₃₋₁₀ cycloalkyl group, R⁴ represents ahydrogen atom, C₁₋₂₀ alkyl group, optionally substituted C₃₋₁₀cycloalkyl group, C₂₋₂₀ alkenyl group, C₂₋₂₀ alkynyl group, C₁₋₂₀haloalkyl group, C₂₋₂₀ haloalkenyl group, C₂₋₂₀ haloalkynyl group, cyanogroup, nitro group or optionally substituted amino group, R⁵ representsa hydrogen atom, C₁₋₂₀ alkyl group, acyl group, formyl group, C₁₋₂₀alkoxy-C₁₋₂₀ alkyl group, C₂₋₂₀ acyloxy-C₁₋₂₀ alkyl group, C₁₋₂₀alkoxycarbonyl group, C₁₋₂₀ alkylsulfonyl group or optionallysubstituted phenylsulfonyl group, Y represents an oxygen atom or sulfuratom, Z represents a single bond, oxygen atom, sulfur atom or NR⁶(wherein, R⁶ represents a hydrogen atom or C₁₋₃₀ alkyl group), and nrepresents an integer of 0 to 4, and X may be the same or different inthe case n is 2 or more.